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Journal articles on the topic 'Sulfinic acids'

Author: Grafiati

Published: 4 June 2021

Last updated: 27 January 2023

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1

Vicente, Dmistocles A., Danilo Galdino, Marcelo Navarro, and Paulo H. Menezes. "Electrochemical synthesis of sulfonamides in a graphite powder macroelectrode." Green Chemistry 22, no. 16 (2020): 5262–66. http://dx.doi.org/10.1039/d0gc01360a.

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2

And, Chew Lee, and Lamar Fields. "SULFINIC ACIDS AND RELATED COMPOUNDS. 21. PREPARATION OF CRYSTALLINE SULFINIC ESTERS1,2." Phosphorus, Sulfur, and Silicon and the Related Elements 45, no. 1-2 (September 1989): 35–45. http://dx.doi.org/10.1080/10426508908046074.

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3

ZOLLER, U. "ChemInform Abstract: Syntheses of Sulfinic Acids." ChemInform 22, no. 40 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199140281.

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4

Herwig, Jürgen, and Wilhelm Keim. "Palladium complex catalysed synthesis of sulfinic acids, sulfinic acid esters, sulfonic acids and S-alkyl alkanethiosulfonates." Inorganica Chimica Acta 222, no. 1-2 (July 1994): 381–85. http://dx.doi.org/10.1016/0020-1693(94)03911-9.

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5

Lee, Chew, D. Brian Stidham, and Lamar Field. "SULFINIC ACIDS AND RELATED COMPOUNDS. 22. DERIVATIVES OF 2-HYDROXYETHANE SULFINIC ACID1,2." Phosphorus, Sulfur, and Silicon and the Related Elements 47, no. 1-2 (January 1990): 53–59. http://dx.doi.org/10.1080/10426509008046846.

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6

STIRLING, C. J. M. "ChemInform Abstract: Sulfinic Acids and Carboxylic Acids - a Comparison." ChemInform 22, no. 41 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199141299.

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7

Liu, Cong-Rong, and Liang-Hui Ding. "Byproduct promoted regioselective sulfenylation of indoles with sulfinic acids." Organic & Biomolecular Chemistry 13, no. 8 (2015): 2251–54. http://dx.doi.org/10.1039/c4ob02575j.

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8

Ivanova, S., and D. Aleksiev. "Addition of Sulfinic Acids to Methacrylic Derivatives." Phosphorus, Sulfur, and Silicon and the Related Elements 186, no. 1 (December 30, 2010): 38–43. http://dx.doi.org/10.1080/10426501003776947.

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9

Ivanova, Sonya. "Reaction of Sulfinic Acids with Heteroconjugated Alkenes." Phosphorus, Sulfur, and Silicon and the Related Elements 188, no. 11 (September 20, 2013): 1670–74. http://dx.doi.org/10.1080/10426507.2012.760562.

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10

Kotomkin, A., N. Rusakova, V. Turovtsev, Yu Orlov, and E. Chernova. "Scale of the electronegativities of sulfinic acids." Актуальные направления научных исследований XXI века: теория и практика 2, no. 5 (December 2, 2014): 91–94. http://dx.doi.org/10.12737/6759.

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11

KAMIYAMA, TSUTOMU, SABURO ENOMOTO, and MASAMI INOUE. "A novel synthesis of aromatic sulfinic acids." CHEMICAL & PHARMACEUTICAL BULLETIN 36, no. 7 (1988): 2652–53. http://dx.doi.org/10.1248/cpb.36.2652.

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12

Rohde, Morten, and Alexander Senning. "The Synthesis of Naturally Occurring Sulfinic Acids." Sulfur reports 14, no. 1 (October 1993): 391–410. http://dx.doi.org/10.1080/01961779308055020.

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13

Lee, Chew, and Lamar Field. "Sulfinic Acids and Related Compounds 23. Preparation of Sulfinic Acids by the Reaction of Sulfonyl Halides with Thiols." Synthesis 1990, no. 05 (1990): 391–97. http://dx.doi.org/10.1055/s-1990-26884.

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14

Sun, Pengfei, Daoshan Yang, Wei Wei, Min Jiang, Zuli Wang, Liyan Zhang, Hui Zhang, Zhenzhen Zhang, Yu Wang, and Hua Wang. "Visible light-induced C–H sulfenylation using sulfinic acids." Green Chemistry 19, no. 20 (2017): 4785–91. http://dx.doi.org/10.1039/c7gc01891f.

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15

Wei, Wei, Jiangwei Wen, Daoshan Yang, Juan Du, Jinmao You, and Hua Wang. "Catalyst-free direct arylsulfonylation of N-arylacrylamides with sulfinic acids: a convenient and efficient route to sulfonated oxindoles." Green Chem. 16, no. 6 (2014): 2988–91. http://dx.doi.org/10.1039/c4gc00231h.

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16

Yang, Wenchao, Shuai Yang, Pinhua Li, and Lei Wang. "Visible-light initiated oxidative cyclization of phenyl propiolates with sulfinic acids to coumarin derivatives under metal-free conditions." Chemical Communications 51, no. 35 (2015): 7520–23. http://dx.doi.org/10.1039/c5cc00878f.

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17

Griesser, Markus, Jean-Philippe R. Chauvin, and Derek A. Pratt. "The hydrogen atom transfer reactivity of sulfinic acids." Chemical Science 9, no. 36 (2018): 7218–29. http://dx.doi.org/10.1039/c8sc02400f.

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Sulfinic acids are characterized to be very good H-atom donors to each of alkyl and alkoxyl radicals. In order to participate in useful radical chain reactions, the sulfonyl radicals must undergo fast propagating reactions to avoid autoxidation, which is surprisingly rate-limited by the reaction of sulfonyl radicals with oxygen.

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18

Yang, Daoshan, Ben Huang, Wei Wei, Jin Li, Gu Lin, Yaru Liu, Jiehua Ding, Pengfei Sun, and Hua Wang. "Visible-light initiated direct oxysulfonylation of alkenes with sulfinic acids leading to β-ketosulfones." Green Chemistry 18, no. 20 (2016): 5630–34. http://dx.doi.org/10.1039/c6gc01403h.

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19

Srivastava, Pramod K., and Lamar Field. "SULFINIC ACIDS AND RELATED COMPOUNDS. 15. CONVENIENT METHODS FOR ESTERIFYING SENSITIVE SULFINIC ACID SALTS1." Phosphorus and Sulfur and the Related Elements 25, no. 2 (November 1985): 161–65. http://dx.doi.org/10.1080/03086648508072729.

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20

Wei, Wei, Jiangwei Wen, Daoshan Yang, Min Wu, Jinmao You, and Hua Wang. "Iron-catalyzed direct difunctionalization of alkenes with dioxygen and sulfinic acids: a highly efficient and green approach to β-ketosulfones." Org. Biomol. Chem. 12, no. 39 (2014): 7678–81. http://dx.doi.org/10.1039/c4ob01369g.

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21

Zhang, Yicheng, Wei Chen, Xueshun Jia, Lei Wang, and Pinhua Li. "A visible-light-induced oxidative cyclization of N-propargylanilines with sulfinic acids to 3-sulfonated quinoline derivatives without external photocatalysts." Chemical Communications 55, no. 19 (2019): 2785–88. http://dx.doi.org/10.1039/c8cc10235j.

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22

Petersen, Jeffrey L., Adenike A. Otoikhian, Moshood K. Morakinyo, and Reuben H. Simoyi. "Organosulfur oxoacids. Part 2. A novel dimethylthiourea metabolite — Synthesis and characterization of the surprisingly stable and inert dimethylaminoiminomethane sulfonic acid." Canadian Journal of Chemistry 88, no. 12 (December 2010): 1247–55. http://dx.doi.org/10.1139/v10-125.

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A new metabolite of the biologically active thiocarbamide dimethylthiourea (DMTU) has been synthesized and characterized. DMTU’s metabolic activation in the physiological environment is expected to be dominated by S-oxygenation, which produces, successively, the sulfenic, sulfinic, and sulfonic acids before forming sulfate and dimethylurea. Only the sulfinic and sulfonic acids are stable enough to be isolated. This manuscript reports on the first synthesis, isolation, and characterization of the sulfonic acid: dimethylaminoiminomethanesulfonic acid (DMAIMSOA). It crystallizes in the orthorhombic Pbca space group and exists as a zwitterion in its solid crystal form. The negative charge is delocalized over the sulfonic acid oxygens and the positive charge is concentrated over the planar N–C–N framework rather than strictly on the sp2-hybridized cationic carbon center. As opposed to its sulfinic acid analogue, DMAIMSOA is extremely inert in acidic environments and can maintain its titer for weeks at pH 6 and below. It is, however, reasonably reactive at physiological pH conditions and can be oxidized to dimethylurea and sulfate by mild oxidants such as aqueous iodine.

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23

Wei, Wei, Jiangwei Wen, Daoshan Yang, Huijun Jing, Jinmao You, and Hua Wang. "Direct difunctionalization of alkynes with sulfinic acids and molecular iodine: a simple and convenient approach to (E)-β-iodovinyl sulfones." RSC Advances 5, no. 6 (2015): 4416–19. http://dx.doi.org/10.1039/c4ra13998d.

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24

Fu, Hong, Jia-Qi Shang, Tao Yang, Yuehai Shen, Chuan-Zhu Gao, and Ya-Min Li. "Copper-Catalyzed Decarboxylative Disulfonylation of Alkynyl Carboxylic Acids with Sulfinic Acids." Organic Letters 20, no. 2 (January 9, 2018): 489–92. http://dx.doi.org/10.1021/acs.orglett.7b03922.

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25

Moon, Youngtaek, Yonghoon Moon, Hangyeol Choi, and Sungwoo Hong. "Metal- and oxidant-free S–P(O) bond construction via direct coupling of P(O)H with sulfinic acids." Green Chemistry 19, no. 4 (2017): 1005–13. http://dx.doi.org/10.1039/c6gc03285k.

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26

Zhou, Nengneng, Meixia Wu, Man Zhang, Xiaoqiang Zhou, and Wei Zhou. "TBPB-initiated cascade cyclization of 3-arylethynyl-[1,1′-biphenyl]-2-carbonitriles with sulfinic acids: access to sulfone-containing cyclopenta[gh]phenanthridines." Organic & Biomolecular Chemistry 18, no. 9 (2020): 1733–37. http://dx.doi.org/10.1039/d0ob00119h.

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27

Angelo, A. C. D., and N. R. Stradiotto. "Electrochemical Reduction of Aromatic Sulfinic Acids in Dimethylsulfoxide." Journal of The Electrochemical Society 144, no. 3 (March 1, 1997): 773–78. http://dx.doi.org/10.1149/1.1837488.

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28

DRABOWICZ, J., P. KIELBASINSKI, and M. MIKOLAJCZYK. "ChemInform Abstract: Sulfinic Acids and Esters in Synthesis." ChemInform 22, no. 40 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199140286.

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29

Aziz, Jessy, Samir Messaoudi, Mouad Alami, and Abdallah Hamze. "Sulfinate derivatives: dual and versatile partners in organic synthesis." Org. Biomol. Chem. 12, no. 48 (2014): 9743–59. http://dx.doi.org/10.1039/c4ob01727g.

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Recent advances in the preparation and synthetic uses of sulfinic acids and their derivatives are highlighted in this review. They are used as versatile partners in sulfonylative and desulfitative reactions.

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30

Sharafi-Kolkeshvandi, Mahnaz, Davood Nematollahi, Farzad Nikpour, and Eslam Salahifar. "Electrochemical synthesis of 1-N-phenyl-4-(sulfonyl)benzene-1,2-diamine derivatives: a mild and regioselective protocol." New Journal of Chemistry 40, no. 6 (2016): 5442–47. http://dx.doi.org/10.1039/c5nj03514g.

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Regioselective synthesis of 1-N-phenyl-4-(arylsulfonyl)benzene-1,2-diamine derivatives was carried out by the electrochemical oxidation of 2-aminodiphenylamine in aqueous solution in the presence of sulfinic acids as nucleophiles.

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31

Chen, Fei, Neng-Neng Zhou, Jun-Long Zhan, Bing Han, and Wei Yu. "tert-Butyl nitrite-mediated vicinal sulfoximation of alkenes with sulfinic acids: a highly efficient approach toward α-sulfonyl ketoximes." Organic Chemistry Frontiers 4, no. 1 (2017): 135–39. http://dx.doi.org/10.1039/c6qo00535g.

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A novel vicinal sulfoximation of alkenes was achieved under mild and metal-free conditions by using readily available sulfinic acids as the sulfonating agent and tert-butyl nitrite (TBN) as the radical initiator and the oxime source.

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32

Li, Luan-Ying, Bo-Rong Leng, Jia-Zhuo Li, Qing-Quan Liu, Jianguang Yu, Ping Wei, De-Cai Wang, and Yi-Long Zhu. "Palladium-catalyzed regioselective hydrosulfonylation of allenes with sulfinic acids." RSC Advances 12, no. 14 (2022): 8443–48. http://dx.doi.org/10.1039/d1ra09036d.

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A simple palladium-based catalytic system for hydrosulfonylation of allenamides was established. Various nitrogen-containing linear allylic sulfones can be generated in moderate to excellent yield with E-selectivity and 100% atom utilization.

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33

ROHDE, M., and A. SENNING. "ChemInform Abstract: The Synthesis of Naturally Occurring Sulfinic Acids." ChemInform 25, no. 40 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199440271.

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34

Lo Conte, Mauro, and Kate S. Carroll. "Chemoselective Ligation of Sulfinic Acids with Aryl-Nitroso Compounds." Angewandte Chemie 124, no. 26 (May 29, 2012): 6608–11. http://dx.doi.org/10.1002/ange.201201812.

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35

Lo Conte, Mauro, and Kate S. Carroll. "Chemoselective Ligation of Sulfinic Acids with Aryl-Nitroso Compounds." Angewandte Chemie International Edition 51, no. 26 (May 29, 2012): 6502–5. http://dx.doi.org/10.1002/anie.201201812.

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36

Meesin, Jatuporn, Praewpan Katrun, Vichai Reutrakul, Manat Pohmakotr, Darunee Soorukram, and Chutima Kuhakarn. "Decarboxylative sulfonylation of arylpropiolic acids with sulfinic acids: synthesis of (E)-vinyl sulfones." Tetrahedron 72, no. 11 (March 2016): 1440–46. http://dx.doi.org/10.1016/j.tet.2016.01.042.

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37

Chauvin, Jean-Philippe R., and Derek A. Pratt. "On the Reactions of Thiols, Sulfenic Acids, and Sulfinic Acids with Hydrogen Peroxide." Angewandte Chemie International Edition 56, no. 22 (December 9, 2016): 6255–59. http://dx.doi.org/10.1002/anie.201610402.

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38

Chauvin, Jean-Philippe R., and Derek A. Pratt. "On the Reactions of Thiols, Sulfenic Acids, and Sulfinic Acids with Hydrogen Peroxide." Angewandte Chemie 129, no. 22 (December 9, 2016): 6351–55. http://dx.doi.org/10.1002/ange.201610402.

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39

Lu, Hongjian, Zheng Lu, and Mingzhou Shang. "Organic Sulfinic Acids and Salts in Visible Light-Induced Reactions." Synthesis 54, no. 05 (October 17, 2021): 1231–49. http://dx.doi.org/10.1055/a-1671-0085.

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AbstractSulfinic acids and their salts are a useful source of sulfur-containing structures. Photocatalysis of these compounds with visible light enables to achieve various transformations under mild conditions. This review summarizes visible-light-induced reactions of sulfinic acids and their salts. It is organized by reaction type and brief discussions on plausible reaction mechanisms for typical transformations are presented.1 Introduction2 Sulfonylation Reactions2.1 Sulfonylation of Alkenes2.2 Sulfonylation of Alkynes2.3 Sulfonylation of Arenes2.4 sp3 C–H Functionalization3 Desulfonylation Reactions4 Sulfenylation Reactions4.1 Sulfenylation of Heteroarenes4.2 Sulfenylation of Carbonyl Chlorides5 Conclusions

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40

Bao, Ruwei, Yanping Feng, Danfeng Deng, Dayun Huang, and Xiangyu Sun. "Sulfinic Acids in Organic Synthesis: A Review of Recent Studies." Asian Journal of Organic Chemistry 10, no. 8 (July 9, 2021): 1884–96. http://dx.doi.org/10.1002/ajoc.202100331.

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41

Blanco, José M., Olga Caamaño, Ana Eirín, Franco Fernández, and Lucia Medina. "Synthesis of Chiral Sulfinic Acids: Sodium(1S-exo)-2-Bornanesulfinate." Synthesis 1990, no. 07 (1990): 584–86. http://dx.doi.org/10.1055/s-1990-26948.

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42

Bondarenko, Oxana B., Lyudmila G. Saginova, and Nikolai V. Zyk. "Synthesis and properties of sultines, cyclic esters of sulfinic acids." Russian Chemical Reviews 65, no. 2 (February 28, 1996): 147–66. http://dx.doi.org/10.1070/rc1996v065n02abeh000204.

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43

Honda, Masanori, Hiromasa Morita, and Isao Nagakura. "Deprotection of Allyl Groups with Sulfinic Acids and Palladium Catalyst." Journal of Organic Chemistry 62, no. 25 (December 1997): 8932–36. http://dx.doi.org/10.1021/jo971194c.

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44

PIHLAJA, K. "ChemInform Abstract: Mass Spectra of Sulfinic Acids, Esters and Derivatives." ChemInform 22, no. 43 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199143299.

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45

Vasil'eva, T. P., and V. V. Znamenskii. "Synthesis and radioprotective properties of 2-arylethylammonium salts of sulfinic acids." Pharmaceutical Chemistry Journal 28, no. 1 (January 1994): 47–50. http://dx.doi.org/10.1007/bf02218953.

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46

Nematollahi, Davood, Mahsa Joudaki, Sadegh Khazalpour, and Firozeh Pouladi. "Electrochemical Oxidation of Sulfinic Acids: Efficient Oxidative Synthesis of Diaryl Disulfones." Journal of The Electrochemical Society 164, no. 6 (2017): G65—G70. http://dx.doi.org/10.1149/2.1111706jes.

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47

NUDELMAN, A. "ChemInform Abstract: Sulfinic Acids and Their Derivatives. Stereochemistry and Chiroptical Properties." ChemInform 22, no. 40 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199140280.

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48

Liu, Cong-Rong, and Liang-Hui Ding. "ChemInform Abstract: Byproduct Promoted Regioselective Sulfenylation of Indoles with Sulfinic Acids." ChemInform 46, no. 26 (June 2015): no. http://dx.doi.org/10.1002/chin.201526145.

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49

Morishita, Wade, and Bradley E. Alger. "Evidence for Endogenous Excitatory Amino Acids as Mediators in DSI of GABAAergic Transmission in Hippocampal CA1." Journal of Neurophysiology 82, no. 5 (November 1, 1999): 2556–64. http://dx.doi.org/10.1152/jn.1999.82.5.2556.

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Depolarization-induced suppression of inhibition (DSI) is a process whereby brief ∼1-s depolarization to the postsynaptic membrane of hippocampal CA1 pyramidal cells results in a transient suppression of GABAAergic synaptic transmission. DSI is triggered by a postsynaptic rise in [Ca2+]in and yet is expressed presynaptically, which implies that a retrograde signal is involved. Recent evidence based on synthetic metabotropic glutamate receptor (mGluR) agonists and antagonists suggested that group I mGluRs take part in the expression of DSI and raised the possibility that glutamate or a glutamate-like substance is the retrograde messenger in hippocampal CA1. This hypothesis was tested, and it was found that the endogenous amino acidsl-glutamate (l-Glu) and l-cysteine sulfinic acid (l-CSA) suppressed GABAA-receptor–mediated inhibitory postsynaptic currents (IPSCs) and occluded DSI, whereas l-homocysteic acid (l-HCA) and l-homocysteine sulfinic acid (l-HCSA) did not. Activation of metabotropic kainate receptors with kainic acid (KA) reduced IPSCs; however, DSI was not occluded. When iontophoretically applied, both l-Glu andl-CSA produced a transient IPSC suppression similar in magnitude and time course to that observed during DSI. Both DSI and the actions of the amino acids were antagonized by (S)-α-methyl-4-carboxyphenylglycine ([S]-MCPG), indicating that the effects of the endogenous agonists were produced through activation of mGluRs. Blocking excitatory amino acid transport significantly increased DSI and the suppression produced by l-Glu orl-CSA without affecting the time constant of recovery from the suppression. Similar to DSI, IPSC suppression by l-Glu or l-CSA was blocked by N-ethylmaleimide (NEM). Moreover, paired-pulse depression (PPD), which is unaltered during DSI, is also not significantly affected by the amino acids. Taken together, these results support the glutamate hypothesis of DSI and argue that l-Glu or l-CSA are potential retrograde messengers in CA1.

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50

Ren, Hexiang, Yuanyang Mu, Ming Zhang, and Ai Qin Zhang. "Synthesis of 3-Phenylsulfonylcoumarins by Cyclisation of Phenyl Propiolates with Sulfinic Acids or Sodium Sulfinates." Journal of Chemical Research 42, no. 10 (October 2018): 515–20. http://dx.doi.org/10.3184/174751918x15385227785338.

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Methods for the synthesis of 3-phenylsulfonylcoumarins by radical sulfonylation cyclisation of phenyl propiolates with sulfinic acids or sodium sulfinates as sulfonyl sources have been developed. A combination of potassium persulfate as oxidant and silver nitrate as catalyst, or tert-butyl hydroperoxide as oxidant and potassium iodide as catalyst were used. The products were formed by an ipso-cyclisation/1,2-ester migration mechanism. The toleration of functional groups is broad and the yield is up to 96%.

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