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Journal articles on the topic 'Allyl methyl sulfide'

Author: Grafiati

Published: 4 June 2021

Last updated: 4 February 2022

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1

Suarez, F., J. Springfield, J. Furne, and M. Levitt. "Differentiation of mouth versus gut as site of origin of odoriferous breath gases after garlic ingestion." American Journal of Physiology-Gastrointestinal and Liver Physiology 276, no. 2 (February 1, 1999): G425—G430. http://dx.doi.org/10.1152/ajpgi.1999.276.2.g425.

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Utilizing the sulfur-containing gases of garlic as probes, we investigated the gut versus mouth origin of odoriferous breath gases. Five individuals ingested 6 g of garlic, and sulfur gases in mouth, alveolar air, and urine samples were measured. The mouth normally contained low concentrations of hydrogen sulfide, methanethiol, and dimethyl sulfide. Immediately after garlic ingestion, transient high concentrations of methanethiol and allyl mercaptan and lesser concentrations of allyl methyl sulfide (AMS), allyl methyl disulfide, and allyl disulfide were observed. With the exception of AMS, all gases were present in far greater concentrations in mouth than alveolar air, indicating an oral origin. Only AMS was of gut origin as evidenced by similar partial pressures in mouth, alveolar air, and urine. After 3 h, AMS was the predominant breath sulfur gas. The unique derivation of AMS from the gut is attributable to the lack of gut and liver metabolism of this gas versus the rapid metabolism of the other gases. Breath odor after garlic ingestion initially originates from the mouth and subsequently from the gut.

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2

Shimizu, Katsumasa, Yuichi Maeda, Kenji Osawa, and Susumu Shimura. "Deodorizing Effect of Rubus suavissimus Extract against Allyl Methyl Sulfide." NIPPON SHOKUHIN KAGAKU KOGAKU KAISHI 51, no. 4 (2004): 205–9. http://dx.doi.org/10.3136/nskkk.51.205.

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3

FANTONI, A. C. "ChemInform Abstract: Microwave Spectrum, Conformation and Internal Rotation in Allyl Methyl Sulfide." ChemInform 22, no. 19 (August 23, 2010): no. http://dx.doi.org/10.1002/chin.199119045.

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4

KYUNG, K. H., and H. P. FLEMING. "Antimicrobial Activity-of Sulfur Compounds Derived from Cabbage‡." Journal of Food Protection 60, no. 1 (January 1, 1997): 67–71. http://dx.doi.org/10.4315/0362-028x-60.1.67.

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Selected sulfur compounds found in cabbage and its fermentation product, sauerkraut, were tested for minimum inhibitory concentration (MIC) against growth of 15 species of bacteria and 4 species of yeasts. S-Methyl-l-cysteine sulfoxide, sinigrin, and dimethyl sulfide at 500 ppm were not inhibitory to any of the bacteria and yeasts tested. Dimethyl disulfide at 500 ppm retarded some, but did not prevent growth of any of the test microorganisms. Dimethyl trisulfide had an MIC to bacteria of 200 ppm and to yeast of 20 ppm. Methyl methanethiosulfinate had an MIC between 50 and 200 ppm for all bacteria, and between 6 and 10 ppm for all yeasts tested. Methyl methanethiosulfonate had an MIC between 20 and 100 ppm for bacteria and between 50 and 500 ppm for yeasts. Allyl isothiocyanate had an MIC between 50 and 500 ppm for bacteria and between 1 and 4 ppm for yeasts. Methyl methanethiosulfinate was 10 to 100 times more inhibitory against Listeria monocytogenes at pH values of 5, 6, and 7 and was much less influenced by pH than was sodium benzoate.

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5

Chittezhath, Manesh, and Girija Kuttan. "Radioprotective Activity of Naturally Occurring Organosulfur Compounds." Tumori Journal 92, no. 2 (March 2006): 163–69. http://dx.doi.org/10.1177/030089160609200213.

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The radioprotective effects of naturally occurring sulfur compounds and isothiocyanates such as diallyl sulfide (DAS), diallyl disulfide (DADS), allyl methyl sulfide (AMS), allyl isothiocyanate (AITC) and phenyl isothiocyanate (PITC) have been investigated in whole body irradiated Swiss albino mice. Administration of these sulfur compounds could reduce the serum content of alkaline phosphatase (ALP), which was elevated after irradiation (23.9 ± 1.82 KA units). The elevated liver content of glutamate pyruvate transaminase (GPT) in control animals (76.2 ± 2.2 U/mL) after irradiation was significantly reduced in DAS (58.93 ± 4 U/mL) and AMS (55.7 ± 2.2 U/mL) treated animals. Elevated levels of lipid peroxides in serum and liver of irradiated control animals were also significantly reduced by treatment with these sulfur compounds. The glutathione (GSH) content in liver and intestinal mucosa was drastically reduced after irradiation. All the sulfur compounds and isothiocyanates could effectively enhance the GSH content of intestinal mucosa and liver. Findings at histopathological analysis of the intestine proved to be correlated with the above results.

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6

Park, Hokoon, Nam Hoon Baik, Jae Yeol Lee, Soo Ja Kim, and Won Hoon Ham. "Regio- and stereoselective reactions of (S)-(1-methylpyrrolidin-2-yl)methyl allyl sulfide." Archives of Pharmacal Research 14, no. 4 (December 1991): 364–69. http://dx.doi.org/10.1007/bf02876886.

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7

SHIN, HAN-SEUNG, W. JOHN RODGERS, ENAYAT A. GOMAA, GALE M. STRASBURG, and J. IAN GRAY. "Inhibition of Heterocyclic Aromatic Amine Formation in Fried Ground Beef Patties by Garlic and Selected Garlic-Related Sulfur Compounds." Journal of Food Protection 65, no. 11 (November 1, 2002): 1766–70. http://dx.doi.org/10.4315/0362-028x-65.11.1766.

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The effects of garlic and selected organosulfur compounds (diallyl disulfide, dipropyl disulfide, diallyl sulfide, allyl methyl sulfide, allyl mercaptan, cysteine, and cystine) on the formation of heterocyclic aromatic amines (HAAs) in fried ground beef patties were evaluated. Minced garlic cloves (ca. 4.8 to 16.7%, wt/wt) or organosulfur compounds (0.67 mmol) were added directly to ground beef. Patties (100 g) were fried at 225°C (surface temperature) for 10 min per side. Two patties were fried for each replication, and five replicates were analyzed for each treatment. For each replicate, four subsamples were analyzed (two unspiked subsamples for concentration and two spiked subsamples for the recovery of HAA standards). The volatile sulfur compounds significantly (P < 0.05) reduced concentrations of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine by reductions of 46 to 81%, while average reductions of 35, 22, and 71%, were achieved with cystine, cysteine, and whole garlic, respectively. The volatile sulfur compounds reduced concentrations of 2-amino-3,8-dimethylimidazo [4,5-f] quinoxaline by 34 to 67%, while reductions of 25, 19, and 63% (P < 0.05) were achieved with cystine, cysteine, and whole garlic, respectively. These studies confirm that garlic and some organosulfur compounds have the potential to reduce HAA formation in cooked beef patties.

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8

Díaz, Mario G., Esteban G. Vega‐Hissi, Matias F. Andrada, and Juan C. Garro Martinez. "Scavenging of Hydrogen Peroxide by Allyl Methyl Sulfide and Diallyl Sulfide, Two Garlic Active Compounds: A Theoretical Study." ChemistrySelect 5, no. 11 (March 20, 2020): 3234–42. http://dx.doi.org/10.1002/slct.201904725.

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9

Konieczny, Marek T., Grzegorz Maciejewski, and Wojciech Konieczny. "Selectivity Adjustment in the Cleavage of Allyl Phenyl and Methyl Phenyl Ethers with Boron Trifluoride-Methyl Sulfide Complex." Synthesis, no. 10 (2005): 1575–77. http://dx.doi.org/10.1055/s-2005-865304.

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10

Mohammed, Soheb Anwar, Bugga Paramesha, Himanshu Meghwani, Maramreddy Prasanna Kumar Reddy, Sudheer Kumar Arava, and Sanjay Kumar Banerjee. "Allyl Methyl Sulfide Preserved Pressure Overload-Induced Heart Failure Via Modulation of Mitochondrial Function." Biomedicine & Pharmacotherapy 138 (June 2021): 111316. http://dx.doi.org/10.1016/j.biopha.2021.111316.

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11

Kubota, Naohiro, and Kazuyoshi Kawazu. "ACTIVE SUBSATNCES IN CHINESE CHIVE AND RAKKYO PLANTS FOR BREAKING BUD DORMANCY IN GRAPEVINES." HortScience 27, no. 6 (June 1992): 689b—689. http://dx.doi.org/10.21273/hortsci.27.6.689b.

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We previously found that volatile substances in Chinese chive (Allium tuberosum) and rakkyo (A. chinense) as well as garlic (A. sativum) stimulated budbreak in vines. But the active substances stimulating budbreak in Chinese chive and rakkyo have not yet been identified. The volatile sulfur—containing substances in fresh Chinese chive and rakkyo were identified by GC—MASS. The main volatile substances in Chinese chive and rakkyo were allyl and methyl mercaptans, and dimethyl disulfide, respectively. Cuttings witn a single bud obtained from `Kyoho' vines in dormancy were exposed to vapors of different concentrations of the three compounds for 12 or 24 hr in a desiccator, and they were kept at 25C, mounted on styrofoam plate floated in water. Diallyl disulfide, a main component in garlic, was also tested for comparison. Irrespective of concentrations and exposure periods of sulfide compounds, sprouting was greatly accelerated with diallyl disulfide. In mercaptan homologues, allyl mercaptan accelerated sprouting more effectively than in methyl mercaptan. A solution of 75% dimethyl disulfide accelerated sprouting on exposure for 12 hr, while inhibited budbreak for 24 hr.

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12

Plaszkó, Tamás, Zsolt Szűcs, Zoltán Kállai, Hajnalka Csoma, Gábor Vasas, and Sándor Gonda. "Volatile Organic Compounds (VOCs) of Endophytic Fungi Growing on Extracts of the Host, Horseradish (Armoracia rusticana)." Metabolites 10, no. 11 (November 8, 2020): 451. http://dx.doi.org/10.3390/metabo10110451.

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The interaction between plant defensive metabolites and different plant-associated fungal species is of high interest to many disciplines. Volatile organic compounds (VOCs) are natural products that are easily evaporated under ambient conditions. They play a very important role in inter-species communication of microbes and their hosts. In this study, the VOCs produced by 43 different fungal isolates of endophytic and soil fungi during growth on horseradish root (Armoracia rusticana) extract or malt extract agar were examined, by using headspace-gas chromatography-mass spectrometry (headspace-GC-MS) and a high relative surface agar film as a medium. The proposed technique enabled sensitive detection of several typical VOCs (acetone, methyl acetate, methyl formate, ethyl acetate, methyl butanol isomers, styrene, beta-phellandrene), along with glucosinolate decomposition products, including allyl cyanide and allyl isothiocyanate and other sulfur-containing compounds—carbon disulfide, dimethyl sulfide. The VOC patterns of fungi belonging to Setophoma, Paraphoma, Plectosphaerella, Pyrenochaeta, Volutella, Cadophora, Notophoma, and Curvularia genera were described for the first time. The VOC pattern was significantly different among the isolates. The pattern was indicative of putative myrosinase activity for many tested isolates. On the other hand, endophytes and soil fungi as groups could not be separated by VOC pattern or intensity.

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13

Kim, Jin Ah, Dong Youl Yoon, and Jin-Chul Kim. "Oxidation-Triggerable Liposome Incorporating Poly(Hydroxyethyl Acrylate-co-Allyl methyl sulfide) as an Anticancer Carrier of Doxorubicin." Cancers 12, no. 1 (January 10, 2020): 180. http://dx.doi.org/10.3390/cancers12010180.

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Since cancer cells are oxidative in nature, anti-cancer agents can be delivered to cancer cells specifically without causing severe normal cell toxicity if the drug carriers are designed to be sensitive to the intrinsic characteristic. Oxidation-sensitive liposomes were developed by stabilizing dioleoylphosphatidyl ethanolamine (DOPE) bilayers with folate-conjugated poly(hydroxyethyl acrylate-co-allyl methyl sulfide) (F-P(HEA-AMS)). The copolymer, synthesized by a free radical polymerization, was surface-active but lost its surface activity after AMS unit was oxidized by H2O2 treatment. The liposomes with F-P(HEA-AMS) were sensitive to H2O2 concentration (0%, 0.5%, 1.0%, and 2.0%) in terms of release, possibly because the copolymer lost its surface activity and its bilayer-stabilizing ability upon oxidation. Fluorescence-activated cell sorting (FACS) and confocal laser scanning microscopy (CLSM) revealed that doxorubicin (DOX)-loaded liposomes stabilized with folate-conjugated copolymers markedly promoted the transport of the anti-cancer drug to cancer cells. This was possible because the liposomes were readily translocated into the cancer cells via receptor-mediated endocytosis. This liposome would be applicable to the delivery carrier of anticancer drugs.

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14

Sami, Rokayya, Abeer Elhakem, Mona Alharbi, Manal Almatrafi, Nada Benajiba, Taha Ahmed Mohamed, Mohammad Fikry, and Mahmoud Helal. "In-Vitro Evaluation of the Antioxidant and Anti-Inflammatory Activity of Volatile Compounds and Minerals in Five Different Onion Varieties." Separations 8, no. 5 (May 1, 2021): 57. http://dx.doi.org/10.3390/separations8050057.

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Onions contain high antioxidants compounds that fight inflammation against many diseases. The purpose was to investigate some selected bioactive activities of onion varieties (Yellow, Red, Green, Leek, and Baby). Antioxidant assays and anti-inflammatory activities such as NO production with the addition of some bioactive components were determined and analyzed by using a spectrophotometer. Gas chromatography and mass spectrometry (GC–MS) was used for the volatile compounds, while an Atomic absorption spectrometer was used for mineral determinations. Red variety achieved the highest antioxidant activities. The total flavonoids were between (12.56 and 353.53 mg Quercetin/gin dry weight) (dw) and the total phenol was (8.75–25.73 mg/g dw). Leek, Yellow and Green extracts achieved highly anti-inflammatory values (3.71–4.01 μg/mL) followed by Red and Baby extracts, respectively. The highest contents of sodium, potassium, zinc, and calcium were established for Red onions. Furfuraldehyde, 5-Methyl-2-furfuraldehyde, 2-Methyl-2-pentenal, and 1-Propanethiol were the most predominant, followed by a minor abundance of the other compounds such as Dimethyl sulfide, Methyl allyl disulfide, Methyl-trans-propenyl-disulfide, and Methyl propyl disulfide. The results recommend that these varieties could act as sources of essential antioxidants and anti-inflammatories to decrease inflammation and oxidative stresses, especially red onions that recorded high activities.

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15

Lawson, Larry D., and Z. Jonathan Wang. "Allicin and Allicin-Derived Garlic Compounds Increase Breath Acetone through Allyl Methyl Sulfide: Use in Measuring Allicin Bioavailability." Journal of Agricultural and Food Chemistry 53, no. 6 (March 2005): 1974–83. http://dx.doi.org/10.1021/jf048323s.

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16

Sujithra, Kathiroli, Subramani Srinivasan, Dhananjayan Indumathi, and Veerasamy Vinothkumar. "Allyl methyl sulfide, an organosulfur compound alleviates hyperglycemia mediated hepatic oxidative stress and inflammation in streptozotocin - induced experimental rats." Biomedicine & Pharmacotherapy 107 (November 2018): 292–302. http://dx.doi.org/10.1016/j.biopha.2018.07.162.

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17

Holland, Herbert L., Cynthia G. Rand, Peter Viski, and Frances M. Brown. "Microbial oxidation of benzyl sulfides and bibenzyl by Mortierella isabellina and Helminthosporium species." Canadian Journal of Chemistry 69, no. 12 (December 1, 1991): 1989–93. http://dx.doi.org/10.1139/v91-287.

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The biotransformation of 1,2-diphenylethane by the fungus Mortierella isabellina ATCC 42613, and that of a series of alkyl benzyl sulfides by the fungi M. isabellina and Helminthosporium species NRRL 4671 have been studied. Mortierella hydroxylates 1,2-diphenylethane in low yield, giving (S)-1,2-diphenylethanol with an enantiomeric purity of 33%. Bioconversions of deuterium-labelled and racemic 1,2-diphenylethanol by M. isabellina demonstrate that this organism performs reversible oxidation/reduction of the alcohol. Biotransformations of n-alkyl benzyl sulfides by H. species give predominantly the (S) enantiomer of sulfoxide, with no sulfone formation, but M. isabellina, although showing a general preference for the oxidation of alkyl benzyl sulfides to (R) sulfoxides, also generates sulfones from n-alkyl benzyl sulfides in a time-dependent manner that suggests a stereoselective removal of (R) sulfoxide. The latter microorganism can be used, however, for the production of (R)-benzyl methyl and benzyl isopropyl sulfoxides, and gives (S)-benzyl tert-butyl sulfoxide in low yield. Key words: biotransformation, enzymes, sulfoxides.

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18

Becker, Petra M., Piet G. van Wikselaar, Monique F. Mul, Arjan Pol, Bas Engel, Jan W. Wijdenes, Carola M. C. van der Peet-Schwering, Henk J. Wisselink, and Norbert Stockhofe-Zurwieden. "Actinobacillus pleuropneumoniae is impaired by the garlic volatile allyl methyl sulfide (AMS) in vitro and in-feed garlic alleviates pleuropneumonia in a pig model." Veterinary Microbiology 154, no. 3-4 (January 2012): 316–24. http://dx.doi.org/10.1016/j.vetmic.2011.07.011.

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19

Ahmad, Mohammad R., Gregg D. Dahlke, and Steven R. Kass. "The Thio-Wittig Rearrangement of Deprotonated Allyl Methyl Sulfide. A Gas-Phase Unimolecular Isomerization Probed with a Variable Temperature Flowing Afterglow-Triple Quadrupole Device." Journal of the American Chemical Society 118, no. 6 (January 1996): 1398–407. http://dx.doi.org/10.1021/ja953116h.

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20

Sujithra, Kathiroli, Subramani Srinivasan, Dhananjayan Indumathi, and Veerasamy Vinothkumar. "Allyl methyl sulfide, a garlic active component mitigates hyperglycemia by restoration of circulatory antioxidant status and attenuating glycoprotein components in streptozotocin-induced experimental rats." Toxicology Mechanisms and Methods 29, no. 3 (November 21, 2018): 165–76. http://dx.doi.org/10.1080/15376516.2018.1534297.

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21

Dr.N.Muninathan, Dr N. Muninathan. "Effect of Paclitaxel along with Di allyl sulfide on Nucleic acid and polyamines changes in 7, 12 Di methyl benz(a) anthracene induced skin cancer wistar rats." IOSR Journal of Dental and Medical Sciences 4, no. 6 (2013): 69–72. http://dx.doi.org/10.9790/0853-0466972.

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22

Meenakshisundaram, Subbiah, and M. Amutha. "Studies on the Oxidation of some Sulfides with Pyridinium Dichromate in Acetonitrile medium." Journal of Chemical Research 23, no. 1 (January 1999): 2–3. http://dx.doi.org/10.1177/174751989902300107.

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The kinetic behaviours of oxidation of dialkyl, alkyl aryl and diphenyl sulfides are quite different with pyridinium dichromate in acetonitrile medium; studies indicate the involvement of a sulfur cation free radical intermediate in diphenyl sulfide oxidation; electron releasing and withdrawing groups retard the reactivity of aryl methyl sulfides; the observed non-linear concave downwards type Hammett plot is well explained by assuming shifts in the rate-limiting step within the same overall reaction pathway.

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23

Ivan, Ignatius, Ignatius Ivan, Maureen Miracle Stella, Maureen Miracle Stella, Kevin Tandarto, Kevin Tandarto, Fanny Budiman, Fanny Budiman, Freggy Spicano Joprang, and Freggy Spicano Joprang. "Plasmodium falciparum Breath Metabolomics (Breathomics) Analysis as a Non-Invasive Practical Method to Diagnose Malaria in Pediatric." Indonesian Journal of Tropical and Infectious Disease 9, no. 1 (April 27, 2021): 24. http://dx.doi.org/10.20473/ijtid.v9i1.24069.

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Children under 5 years of age are particularly vulnerable to malaria. Malaria has caused 445,000 deaths worldwide. Currently, rapid diagnostic tests (RDTs) are the fastest method to diagnose malaria. However, there are limitations that exist such as low sensitivity in detecting infections with low parasitemia. Practical, non-invasive and high ability tests to detect parasite are needed to find specific biomarkers for P. falciparum infection to determine the potential of P. falciparum 4 thioether in breathomics analysis by GC-MS as a practical non-invasive method in diagnosing malaria in pediatrics. Literature reviews from Google Scholar and ProQuest were published no later than the last 5 years. The concept of breathomics is that the breath’s volatile organic compounds (VOCs) profile is altered when the health condition changes. Breath samples from individuals infected with P. falciparum malaria were taken by exhalation. Through GC-MS analysis, it was found that 4 thioether compounds (allyl methyl sulfide (AMS), 1-methylthio-propane, (Z) -1-methylthio-1-propene and (E) -1-methylthio-1-propene) underwent a significant change in concentration during the infection. Based on experiments conducted on mice and humans, the breathomics method is known to be able to detect parasitemia levels up to <100 parasites/µL, has a sensitivity level of about 71% to 91% and a specificity of about 75% to 94%. The discovery of 4 thioether compounds by GC-MS is a strong indication of malaria, because it has the potential for high sensitivity and specificity, and the detection power exceeds the ability of RDTs.

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24

Muninathan, N., Ursula Sampson, Prashanth Talikoti, Uma Maheshwari, Archana, and Kumar. "Effect of paclitaxel along with di allyl sulfide on immuno competent cells, immune complexes and immunoglobulins changes in 7,12 Di Methyl Benz(A) anthracene induced skin cancer in Wistar rats." International Journal of Medical Research & Health Sciences 3, no. 1 (2014): 155. http://dx.doi.org/10.5958/j.2319-5886.3.1.030.

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25

Tian, Juan, Dayong Sang, Xiaodong Tu, Zhoujun He, and Ming Yao. "Cleavage of Catechol Monoalkyl Ethers by Aluminum Triiodide–Dimethyl Sulfoxide." Synthesis 51, no. 03 (September 26, 2018): 704–12. http://dx.doi.org/10.1055/s-0037-1610996.

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Using eugenol and vanillin as model substrates, a practical method is developed for the cleavage o-hydroxyphenyl alkyl ethers. Aluminum oxide iodide (O=AlI), generated in situ from aluminum triiodide and dimethyl sulfoxide, is the reactive ether cleaving species. The method is applicable to catechol monoalkyl ethers as well as normal phenyl alkyl ethers for the removal of methyl, ethyl, isopropyl, and benzyl groups. A variety of functional groups such as alkenyl, allyl, amide, cyano, formyl, keto, nitro, and halogen are well tolerated under the optimum conditions. Partial hydrodebromination was observed during the demethylation of 4-bromoguaiacol, and was resolved using excess DMSO as an acid scavenger. This convenient and efficient procedure would be a practical tool for the preparation of catechols.

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26

Musalov, Maxim V., Vladimir A. Potapov, Vladimir A. Yakimov, Maria V. Musalova, Arkady A. Maylyan, Sergey V. Zinchenko, and Svetlana V. Amosova. "A Regioselective Synthesis of Novel Functionalized Organochalcogen Compounds by Chalcogenocyclofunctionalization Reactions Based on Chalcogen Halides and Natural Products." Molecules 26, no. 12 (June 18, 2021): 3729. http://dx.doi.org/10.3390/molecules26123729.

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The regioselective synthesis of novel functionalized condensed organochalcogen compounds by chalcogenocyclofunctionalization reactions based on chalcogen halides and the natural products thymol and carvacrol has been developed. The reactions of selenium dibromide with allyl thymol and allyl carvacrol proceeded in methylene chloride at room temperature in the presence of NaHCO3 affording bis[(7-isopropyl-4-methyl-2,3-dihydro-1-benzofuran-2-yl)methyl] and bis[(4-isopropyl-7-methyl-2,3-dihydro-1-benzofuran-2-yl)methyl] selenides in 90–92% yield. Similar sulfides were obtained in 70–72% yields by the reaction of sulfur dichloride in chloroform under reflux. Trihalotellanes containing the same organic moieties were synthesized from allyl thymol, allyl carvacrol and tellurium tetrachloride or tetrabromide in quantitative yields. Corresponding functionalized ditellurides were prepared in 91–92% yields by the reduction of the trichlorotellanes with sodium metabisulfite in two-phase solvent system. The comparison of reactivity of sulfur, selenium and tellurium halides in chalcogenocyclofunctionalization and distinguishing features of each reaction were discussed.

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Warden, Andrew C., Stephen C. Trowell, and Murat Gel. "A Miniature Gas Sampling Interface with Open Microfluidic Channels: Characterization of Gas-to-Liquid Extraction Efficiency of Volatile Organic Compounds." Micromachines 10, no. 7 (July 19, 2019): 486. http://dx.doi.org/10.3390/mi10070486.

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Chemosensory protein based olfactory biosensors are expected to play a significant role in next-generation volatile organic compound (VOC) detection systems due to their ultra-high sensitivity and selectivity. As these biosensors can perform most efficiently in aqueous environments, the detection systems need to incorporate a gas sampling interface for gas-to-liquid extraction. This interface should extract the VOCs from the gas phase with high efficiency and transfer them into the liquid containing biosensors to enable subsequent detection. To design such a transfer interface, an understanding of the key parameters influencing the gas-to-liquid extraction efficiency of target VOCs is crucial. This paper reports a gas sampling interface system based on a microfluidic open-channel device for gas-to-liquid extraction. By using this device as a model platform, the key parameters dictating the VOC extraction efficiency were identified. When loaded with 30 μL of capture liquid, the microfluidic device generates a gas-liquid interface area of 3 cm2 without using an interfacial membrane. The pumpless operation based on capillary flow was demonstrated for capture liquid loading and collection. Gas samples spiked with lipophilic model volatiles (hexanal and allyl methyl sulfide) were used for characterization of the VOC extraction efficiency. Decreasing the sampling temperature to 15 °C had a significant impact on increasing capture efficiency, while variation in the gas sampling flow rate had no significant impact in the range between 40–120 mL min−1. This study found more than a 10-fold increase in capture efficiency by chemical modification of the capture liquid with alpha-cyclodextrin. The highest capture efficiency of 30% was demonstrated with gas samples spiked with hexanal to a concentration of 16 ppm (molar proportion). The approach in this study should be useful for further optimisation of miniaturised gas-to-liquid extraction systems and contribute to the design of chemosensory protein-based VOC detection systems.

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Schenk, Wolfdieter A., Bernhard Steinmetz, Michael Hagel, Waldemar Adam, and Chantu R. Saha-Möller. "Oxyfunctionalization of Allyl Thioether Ruthenium Complexes with Dimethyldioxirane." Zeitschrift für Naturforschung B 52, no. 11 (November 1, 1997): 1359–71. http://dx.doi.org/10.1515/znb-1997-1114.

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Abstract Allyl thioether complexes [CpRu(P-P)(SRR′)]PF6 (P-P = Ph2PCH2PPh2 (dppm), Ph2PC2H4PP2 (dppe), R = Me, Et, Ph, R′ = 3-propenyl, 3-cyclohexenyl, 2-methyl-2-buten-4-yl) and [CpRu(chir)(SRR′)]PF6 (chir = (S,S)-Ph2PCHMeCHMePPh2, R = Me, CH2Ph, R′ = 2-methyl-2-buten-4-yl) are obtained from the corresponding thiolate complexes by reaction with the appropriate allyl bromide. Careful oxidation with dimethyldioxirane (DMD) gave the allyl sulfoxide complexes [CpRu(P-P)(MeS(O)CH2CH=CH2)]PF6 (P-P = dppm, dppe). Double oxidation to the corresponding sulfinylmethyl epoxide complexes can be readily achieved with an excess of DMD. Oxidation of the chir complexes proceeds with only moderate diastereoselectivity. The structure of the (R, R/S, S) diastereomer of [CpRu(dppm)(MeS(O)CH2CHCH2O)]PF6 was determined: monoclinic space group P21/c (No. 14), a = 11.21(2), b = 16.762(9), c = 18.45(4) Å, β = 94.4(1)°, Z = 4. For a representative example, the decomplexation of the sulfoxide-epoxide ligand by sodium iodide in acetone was demonstrated.

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29

Lukevics, Edmunds, Edgars Abele, Pavel Arsenyan, Ramona Abele, Kira Rubina, Irina Shestakova, Ilona Domracheva, and Violetta Vologdina. "Synthesis and Cytotoxicity of Silicon Containing Pyridine and Quinoline Sulfides." Metal-Based Drugs 9, no. 1-2 (January 1, 2002): 45–51. http://dx.doi.org/10.1155/mbd.2002.45.

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Silicon containing pyridine and quinoline sulfides have been prepared using phase transfer catalytic system thiol/alkyl halide / solid KOH/18-crown-6 / toluene. The target S-ethers were isolated in yields up to 81%. The cytotoxicity of the synthesized compounds was studied. Among pyridine sulfides S-[3-(1-methyl- 1-silacyclohexyl)propyl] derivatives 5e and 6e exhibit the highest cytotoxicity. Aliphatic silicon derivatives were considerably less active. 8-[(Trimethylsilylmethyl)thio]quinoline (8a) exhibits the highest activity among quinoline sulfides.

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30

Kamerbeek, Nanne M., Arjen J. J. Olsthoorn, Marco W. Fraaije, and Dick B. Janssen. "Substrate Specificity and Enantioselectivity of 4-Hydroxyacetophenone Monooxygenase." Applied and Environmental Microbiology 69, no. 1 (January 2003): 419–26. http://dx.doi.org/10.1128/aem.69.1.419-426.2003.

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ABSTRACT The 4-hydroxyacetophenone monooxygenase (HAPMO) from Pseudomonas fluorescens ACB catalyzes NADPH- and oxygen-dependent Baeyer-Villiger oxidation of 4-hydroxyacetophenone to the corresponding acetate ester. Using the purified enzyme from recombinant Escherichia coli, we found that a broad range of carbonylic compounds that are structurally more or less similar to 4-hydroxyacetophenone are also substrates for this flavin-containing monooxygenase. On the other hand, several carbonyl compounds that are substrates for other Baeyer-Villiger monooxygenases (BVMOs) are not converted by HAPMO. In addition to performing Baeyer-Villiger reactions with aromatic ketones and aldehydes, the enzyme was also able to catalyze sulfoxidation reactions by using aromatic sulfides. Furthermore, several heterocyclic and aliphatic carbonyl compounds were also readily converted by this BVMO. To probe the enantioselectivity of HAPMO, the conversion of bicyclohept-2-en-6-one and two aryl alkyl sulfides was studied. The monooxygenase preferably converted (1R,5S)-bicyclohept-2-en-6-one, with an enantiomeric ratio (E) of 20, thus enabling kinetic resolution to obtain the (1S,5R) enantiomer. Complete conversion of both enantiomers resulted in the accumulation of two regioisomeric lactones with moderate enantiomeric excess (ee) for the two lactones obtained [77% ee for (1S,5R)-2 and 34% ee for (1R,5S)-3]. Using methyl 4-tolyl sulfide and methylphenyl sulfide, we found that HAPMO is efficient and highly selective in the asymmetric formation of the corresponding (S)-sulfoxides (ee > 99%). The biocatalytic properties of HAPMO described here show the potential of this enzyme for biotechnological applications.

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31

Rubina, Kira, Edgars Abele, Pavel Arsenyan, Ramona Abele, Maris Veveris, and Edmunds Lukevics. "Synthesis of Silicon and Germanium Containing Heteroaromatic Sulfides as Cholesterol Level Lowering and Vasodilating Agents." Metal-Based Drugs 8, no. 2 (January 1, 2001): 85–93. http://dx.doi.org/10.1155/mbd.2001.85.

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Silicon and germanium containing heteroaromatic sulfides have been prepared using phase transfer catalytic (PTC) system thiol / Si or Ge containing alkyl halide / solid KOH / 18- crown-6 / toluene. The target sulfides were isolated in yields up to 92 %. It has been found that 2-{[dimethyl (β-triethylgermylethyl)-silylmethyl]thio}-1-methylimidazole and 2-{[dimethyl(β-triphenylsilylethyl) silyl-methyl]thio}benzothiazole are the most active cholesterol level lowering and vasodilating agents.

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32

Kubec, R., M. Hrbáčová, R. A Musah, and J. Velíšek. "Allium discoloration: the nature of onion pinking and garlic greening." Czech Journal of Food Sciences 22, SI - Chem. Reactions in Foods V (January 1, 2004): S109—S112. http://dx.doi.org/10.17221/10629-cjfs.

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Precursors involved in the formation of pink and green-blue pigments during onion and garlic processing, respectively, have been studied. It has been confirmed that the formation of both pigments is of a very similar nature, with (E)-S-(1-propenyl)cysteine sulfoxide (isoalliin) serving as the primary precursor. Upon disruption of the tissue, isoalliin and other S-alk(en)ylcysteine sulfoxides are enzymatically cleaved, yielding prop-1-enylcontaining thiosulfinates [CH<sub>3</sub>CH = CHS(O)SR; R = methyl, allyl, propyl, 1-propenyl], among others. The latter compounds subsequently react with amino acids to produce the pigments. Whereas the onion and leek-related propyl, prop-1-enyl and methyl derivatives can form pink, pink-red and magenta compounds, those containing the allyl group yield dark blue products after reacting with glycine at pH 5.0.

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33

Kantlehner, Willi, Jochen Mezger, Ralf Kreß, Horst Hartmann, Thorsten Moschny, Ioannis Tiritiris, Boyan Iliev, et al. "Orthoamide, LXIX [1]. Beiträge zur Synthese N,N,N´,N´,N´´-peralkylierter Guanidine und N,N,N´,N´,N´´䞲,N´´-persubstituierter Guanidiniumsalze / Orthoamides, LXIX [1]. Contributions to the Synthesis of N, N, N´, N´, N´-peralkylated Guanidines and N, N, N´, N´, N´´, N´´-persubstituted Guanidinium Salts." Zeitschrift für Naturforschung B 65, no. 7 (July 1, 2010): 873–906. http://dx.doi.org/10.1515/znb-2010-0712.

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N, N, N´, N´-Tetraalkyl-chloroformamidinium chlorides 6 are prepared from N, N, N´, N´-tetraalkylureas 5 and phosgene in acetonitrile. The iminium salts 6 react with primary and secondary amines in the presence of triethylamine to give N, N, N´, N´, N´´-pentasubstituted and N, N, N´, N´, N´´, N´´- hexasubstituted guanidinium salts 7 and 8, respectively, Treatment of the guanidinium salts 7 with sodium hydroxide in excess affords the N, N, N´N´, N´´-pentasubstituted guanidines 9a - 9aa. Additionally, the N, N, N´, N´, N´´-pentasubstituted and N, N, N´, N´, N´´, N´´-hexasubstituted guanidinium salts 7l´, 7p´ and 8a - c can be obtained from the reaction mixtures by addition of stoichiometric amounts of sodium hydroxide. A modified method is described for the preparation of guanidinium salts possessing dialkylamino substituents consisting of two long-chain alkyl groups (>C14). Some guanidines 9 were alkylated with allyl chloride and bromide, ethyl bromide, butyl bromide, benzyl bromide and chloride, dimethyl sulfate, diethyl sulfate, and methyl methansulfonate to give the corresponding guanidinium salts 11 - 15. By alkylation of the N, N, N´, N´, N´´-pentasubstituted guanidine 9v with triethyloxonium tetrafluoroborate the guandinium tetrafluoroborate 16a is accessible. N-Functionalized guanidinium salts 17 - 18a - c result from the reaction of N, N, N´, N´, N´´-pentasubstituted guanidines with ethyl bromoacetate and bromoacetonitrile, respectively, and subsequent anion exchange with sodium tetraphenylborate. N, N, N´, N´-Tetramethylguanidine (21) adds to ethyl acrylate to give the labile guanidine 22, which forms the guanidinium salt 23a on treatment with methyl iodide. Zwitterionic guanidinium salts 25 result, when N, N, N´, N´, N´´-pentasubstituted guanidines are treated with sultones 24.

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34

Haynes, RK, AG Katsifis, LM King, and SC Vonwiller. "Aprotic Conjugate Addition Reactions of Lithiated Allylic Sulfoxides With Acyclic Enones; a Breakdown of the trans-Decalyl Transition State." Australian Journal of Chemistry 42, no. 10 (1989): 1785. http://dx.doi.org/10.1071/ch9891785.

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The reactions of lithiated 1-(t-butylsulfinyl)prop-2-ene, 1-(t-butylsulfinyl)-3-methylbut-2-ene, 1-(t-butylsulfinyl)but-2-ene, 1-(phenylsulfinyl)but-2-ene and 2-methyl-1-(phenylsu1finyl)prop- 2-ene with methyl vinyl ketone, mesityl oxide and crotonaldehyde give largely carbonyl addition products arising from reaction through C1 or C3 of the allyl system. In the case of methyl crotonate, conjugate addition through C3 is observed. The initially formed diastereomers of the C1 adducts, allylic sulfoxides, are configurationally unstable. Only the lithiated 1-(t-butylsulfinyl)-3-methylbut-2-ene undergoes conjugate addition with methyl vinyl ketone to give an (E)-vinyl sulfoxide whose formation may involve the trans-decalyl transition state characteristic of the reactions of lithiated allylic sulfoxides with cyclic enones.

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35

Islam, Kobirul, R. Sidick Basha, Ajaz A. Dar, Deb K. Das, and Abu T. Khan. "A direct approach for the expedient synthesis of unsymmetrical ethers by employing bromodimethylsulfonium bromide (BDMS) mediated C–S bond cleavage of naphthalene-2-ol sulfides." RSC Advances 5, no. 97 (2015): 79759–64. http://dx.doi.org/10.1039/c5ra14563e.

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36

Holoch, Jan, and Wolfgang Sundermeyer. "Übermethyl-halogenierte Allyl-methyl-sulfoxide und -sulfone und die Darstellung halogenierter Sulfine." Chemische Berichte 119, no. 1 (January 1986): 269–78. http://dx.doi.org/10.1002/cber.19861190124.

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37

Mikhailova, T. V., T. A. Misharina, A. F. Aérov, V. A. Lyapin, A. I. Gren', L. E. Vysotskaya, and R. V. Golovnya. "Gas-chromatographic characteristics of 2-methyl-2-propenyl alkyl sulfides." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 36, no. 7 (July 1987): 1407–10. http://dx.doi.org/10.1007/bf01557512.

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38

Zhang, Qiao Y., Xin J. Cheng, Xin Y. Zhao, La M. Wu, Long F. Jin, and Hui J. Zhang. "Combined Alkylating Agents as a Resolution for Highly Selective N-Alkylation of 2-Hydroxybenzaldehyde Acylhydrazones." Synlett 30, no. 11 (May 8, 2019): 1334–38. http://dx.doi.org/10.1055/s-0037-1611823.

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Although 2-hydroxybenzaldehyde acylhydrazones, such as salicylaldehyde acylhydrazones, are intriguing bioactive molecules, few of their N-alkylated derivatives are known, and only methyl analogues have been reported previously. We achieved selective N-alkylation of 2-hydroxybenzaldehyde acylhydrazones, as their Fe(III) complexes, by using combinations of alkylating agents (for example, an alkyl bromide and a dialkyl sulfate). Fifteen substrates were examined, and 45 new 2-hydroxybenzaldehyde acyl(alkyl)hydrazones were synthesized in moderate to good yields. In all cases, the target products were obtained exclusively, and no O-alkylation byproducts were produced. The method provides an efficient way of preparing 2-hydroxybenzaldehyde acyl(alkyl)hydrazones.

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39

Wang, Qiang, Shi Dong Wang, Ming Chen Qi, and Shu Liang Zang. "Synthesis and Characterization of Alkeyl Imidazolium Ionic Liquids." Advanced Materials Research 1048 (October 2014): 452–55. http://dx.doi.org/10.4028/www.scientific.net/amr.1048.452.

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Two new imidazole ionic liquid salts, 1-allyl-3-methylimidazolium chloride ([AMIM]Cl) and 1-allyl-3-methy-imidazolium hydrogen sulfate ([EMIM]HSO4), were synthesized with direct synthesis and two-step synthesis method, using a viscosity meter, PH meter, conductivity meter, densitometer, infrared spectrometer determined its chemical structure and properties. The results show that two ionic liquids in the range is slightly different, the trend is roughly same. As the temperature increases, the viscosity decreases, PH gradually increased, the density decreases slightly, can be regarded as constant, the conductivity gradually increased. Ionic liquids of the two IR spectra analysis show its structure and synthetic route consistent with the structure of matter.

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40

Yamamoto, Tamotsu, Tetsushi Hayakawa, Mugi Yoshino, Soh-Ichiroh Hata, and Yorinobu Hirayama. "AN EFFICIENT OXIDATION OF LONG CHAIN ALKYL METHYL SULFIDES TO SULFOXIDES." Organic Preparations and Procedures International 32, no. 2 (April 2000): 192–96. http://dx.doi.org/10.1080/00304940009356286.

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41

Steel, BJ, AS Kayaalp, T. Kurucsev, AD Ward, and MB Jackson. "Nitrate Selectivity of Ion-Exchange Resins and of Their Model Compounds. I. Conductance Measurements on Benzyltrialkylammonium Salts." Australian Journal of Chemistry 43, no. 12 (1990): 1983. http://dx.doi.org/10.1071/ch9901983.

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The concentration dependence of the conductance in aqueous solution of a series of benzyltrialkylammonium chlorides, nitrates and sulfates was measured. The n-alkyl substituents in this series were methyl, ethyl, propyl , butyl and pentyl. The conductances of the chlorides, nitrates and sulfates fit satisfactorily the electrostatic ion pairing models relevant to 1 : 1 and 1 : 2 electrolytes. The extent of ion pairing is small in all the solutions studied but consistently larger for nitrates and sulfates compared with chlorides. The dependence of the association constants on the alkyl substitutents shows different trends for the monovalent anions compared with the sulfate salts.

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42

Schaefer, Ted, Glenn H. Penner, Kerry J. Davie, and Rudy Sebastian. "Control of the orientation of the aldehyde group in 2-(alkylthio)benzaldehydes by the directional lone-pair on sulfur." Canadian Journal of Chemistry 63, no. 3 (March 1, 1985): 777–81. http://dx.doi.org/10.1139/v85-128.

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The 1H nmr spectral parameters for 2-alkylthio derivatives benzaldehyde (alkyl = CH3, CH2CH3, CH(CH3)2, C(CH3)3) are used to show that the O-syn conformation of the aldehyde group decreases from 40% for the methyl to zero for the tert-butyl compound in CC14 solution at about 300 K. It appears that the alkylthio groups twist out of the benzene plane to the same extent as in the alkyl phenyl sulfides and that it is the concomitant approaches of the 3p lone-pairs on sulfur into the ring plane which, by repulsive interactions with the C=O bond, determine the conformations of the aldehyde group. The spectral parameters display interesting changes as the size of the alkyl group increases. For example, the chemical shift of the aldehydic proton is larger than that reported for any other benzaldehyde derivative in CCl4 solution.

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43

Schwärzler, Alexander, Gerhard Laus, Volker Kahlenberg, Klaus Wurst, Thomas Gelbrich, Christoph Kreutz, Holger Kopacka, Günther Bonn, and Herwig Schottenberger. "Quaternary 4-Amino-1,2,4-triazolium Salts: Crystal Structures of Ionic Liquids and N-Heterocyclic Carbene (NHC) Complexes." Zeitschrift für Naturforschung B 64, no. 6 (June 1, 2009): 603–16. http://dx.doi.org/10.1515/znb-2009-0604.

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Quaternary salts were prepared by reaction of 4-amino-1,2,4-triazole and 4-amino-3,5-dialkyl- 1,2,4-triazoles (alkyl = Me, Et) with dimethyl and diethyl sulfate at ambient temperature. Subsequent ion metathesis gave hexafluorophosphates and bis(trifluoromethylsulfonyl)imides as crystalline derivatives or ionic liquids.Methylation at 100 ◦C gave the 4-(dimethylamino)-1-methyl-1,2,4- triazolium salt, a precursor for a new carbene ligand which was incorporated into Ag and Rh complexes. The synthesis of 5-bromo-4-(dimethylamino)-1-methyl-1,2,4-triazolium hexafluorophosphate is also reported. Crystal structures of fourteen compounds have been determined by X-ray diffraction

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44

Brownlee, B. G., S. L. Kenefick, G. A. MacInnis, and S. E. Hrudey. "Characterization of odorous compounds from bleached kraft pulp mill effluent." Water Science and Technology 31, no. 11 (June 1, 1995): 35–40. http://dx.doi.org/10.2166/wst.1995.0396.

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Odour compounds in extracts of bleached kraft pulp mill effluent (BKME) have been characterized by olfactory gas chromatography (OGC) and gas chromatography-mass spectrometry. A variety of sulfury odours was detected by OGC in addition to woody and pulp mill-like odours. Three sulfur compounds were identified by comparison of retention times and partial mass spectra with authentic standards: dimethyl disulfide, 3-methylthiophene and thioanisole (methyl phenyl sulfide). Typical concentrations in BKME were 1, 0.05, and 0.5 μg/l, respectively. Their odour intensity is relatively low and they were not detected by OGC. Dimethyl trisulfide was tentatively identified by comparison of its partial mass spectrum with a literature (library) spectrum. Its concentration in BKME was estimated at 0.5-2 μg/l. It corresponded to a skunky odour in the OGC profiles. Efforts to identify another odour peak, eluting just after 3-methylthiophene, with a pronounced alkyl sulfide odour were unsuccessful.

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45

Wijayanti, Mahardika Agus, Eti Nurwening Sholikhah, Ruslin Hadanu, Jumina Jumina, Supargiyono Supargiyono, and Mustofa Mustofa. "Additive In Vitro Antiplasmodial Effect of N-Alkyl and N-Benzyl-1,10-Phenanthroline Derivatives and Cysteine Protease Inhibitor E64." Malaria Research and Treatment 2010 (June 22, 2010): 1–8. http://dx.doi.org/10.4061/2010/540786.

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Potential new targets for antimalarial chemotherapy include parasite proteases, which are required for several cellular functions during the Plasmodium falciparum life cycle. Four new derivatives of N-alkyl and N-benzyl-1,10-phenanthroline have been synthesized. Those are (1)-N-methyl-1,10-phenanthrolinium sulfate, (1)-N-ethyl-1,10-phenanthrolinium sulfate, (1)-N-benzyl-1,10-phenanthrolinium chloride, and (1)-N-benzyl-1,10-phenanthrolinium iodide. Those compounds had potential antiplasmodial activity with IC50 values from 260.42 to 465.38 nM. Cysteine proteinase inhibitor E64 was used to investigate the mechanism of action of N-alkyl and N-benzyl-1,10-phenanthroline derivatives. A modified fixed-ratio isobologram method was used to study the in vitro interactions between the new compounds with either E64 or chloroquine. The interaction between N-alkyl and N-benzyl-1,10-phenanthroline derivatives and E64 was additive as well as their interactions with chloroquine were also additive. Antimalarial mechanism of chloroquine is mainly on the inhibition of hemozoin formation. As the interaction of chloroquine and E64 was additive, the results indicated that these new compounds had a mechanism of action by inhibiting Plasmodium proteases.

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46

Yao, Hua, Sen Lin, Xiaoyang Zhong, Bingqing Wang, Zhaohua Yan, and Feng Xiong. "H2O2-Promoted Alkylation of Quinoxalin-2(1H)-ones with Styrenes and Dimethyl Sulfoxide." Synlett 32, no. 12 (May 12, 2021): 1213–18. http://dx.doi.org/10.1055/a-1507-6499.

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AbstractA hydrogen peroxide (H2O2)-mediated quinoxaline-2(1H)-ones hydrocarbylation reaction has been reported. The reaction is achieved through the difunctionalization of styrene. In this transformation, methyl radical resulting from dimethyl sulfoxide firstly attacks styrenes to provide alkyl radicals which then undergo alkylation at the C3 position of quinoxalin-2(1H)-one. A green, convenient, and simple protocol for the synthesis of 3-alkylquinoxalin-2(1H)-ones was provided.

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47

Sugihara, Takumichi, Mamiko Yamada, Masahiko Yamaguchi, and Mugio Nishizawa. "The Intra- and Intermolecular Pauson-Khand Reaction Promoted by Alkyl Methyl Sulfides." Synlett 1999, no. 6 (June 1999): 771–73. http://dx.doi.org/10.1055/s-1999-2745.

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48

Sapaev, B., F. E. Saitkulov, A. A. Tashniyazov, and OU Normurodov. "Study of methylation reactions of 2-phenylquinazoline-4-tion with “soft” and “hard” methylation agents and determination of its biological activity." E3S Web of Conferences 258 (2021): 04023. http://dx.doi.org/10.1051/e3sconf/202125804023.

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Alkylation reactions of 2-phenylquinazoline-4-thion with methylation agents “soft” (methyl iodide) and “hard” (dimethyl sulfate, methyltozylate) were studied. It was found that the reaction proceeds with the formation of alkyl products at the N3 - and S4 - reaction centers, depending on the methylation agent, solvent and temperature. This indicated the ambivalent nature of the 2-phenylquinazoline-4-tion anion. Prolongation of the reaction time leaded to the formation of a second isomeric product (VII). A slight increase in phenyl N3-product (VII) yield was noted when dimethyl sulfate and methylfolate were used as methylation agents. In non-polar proton-free solvent DMF and dipolar proton-free solvent acetonitrile, only N-methyl product (VII) was formed because of the reaction. An increase in the polarity of the solvent and the “hardness” of the methylation agent leads to an increase in the yield of N3 products.

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49

Yamamoto, Tamotsu, Tetsushi Hayakawa, Mugi Yoshino, Soh-ichiroh Hata, and Yorinobu Hirayama. "ChemInform Abstract: An Efficient Oxidation of Long Chain Alkyl Methyl Sulfides to Sulfoxides." ChemInform 31, no. 33 (June 3, 2010): no. http://dx.doi.org/10.1002/chin.200033073.

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50

Kerr, William J., David M. Lindsay, Mark McLaughlin, and Peter L. Pauson. "A polymer-supported alkyl methyl sulfide as an efficient promoter of the Khand cyclisation reaction." Chemical Communications, no. 16 (2000): 1467–68. http://dx.doi.org/10.1039/b004568n.

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