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Journal articles on the topic 'Bromohydrins'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Collette, Timothy W., Susan D. Richardson, and Alfred D. Thruston. "Identification of Bromohydrins in Ozonated Waters." Applied Spectroscopy 48, no. 10 (1994): 1181–92. http://dx.doi.org/10.1366/0003702944027471.

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Because ozonation is becoming a popular alternative to chlorination for disinfection of drinking water and little is known about the potential adverse health effects of ozonation disinfection by-products (DBPs), we have sought to identify ozone DBPs, particularly brominated organics, which are of principal concern due to their anticipated toxicity. Using gas chromatography coupled (independently) to low-resolution electron-impact mass spectrometry (LR-EI-MS), high-resolution EI-MS, chemical ionization MS (with 2% ammonia in methane), and Fourier transform infrared spectrometry, we have identif

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2

Macleod, JK, and TF Molinski. "Synthetic Studies on Wedeligenin: Preparation of 3-Hydroxy-Substituted Decalincarbonitriles as a Model for 'A Ring' Annulation." Australian Journal of Chemistry 43, no. 8 (1990): 1309. http://dx.doi.org/10.1071/ch9901309.

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Six new 3-hydroxydecalincarbonitriles were synthesized by employing an annulation strategy involving intramolecular alkylation of 5-bromoalkyl substituted malononitriles or acetonitriles. 2-Allyl-2-methylcyclohexanone was condensed with malononitrile to give the dialkylcyclohexylidenepropanedinitrile (14). Alternatively, Horner-Emmons- Wittig condensation of the same ketone with diethyl cyanomethylphosphonate gave the corresponding acetonitrile (28). Reduction of the dinitrile with sodium borohydride to give a mixture of cis and trans cyclohexyl malononitriles followed by epoxidation of the al

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3

Tsizin, Yu S., E. P. Prokof'ev, and N. L. Sergovskaya. "Bromohydrins of reissert compounds." Chemistry of Heterocyclic Compounds 21, no. 4 (1985): 455–58. http://dx.doi.org/10.1007/bf00504412.

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4

Li, Lezhen, Peijie Cai, Qingxiang Guo, and Song Xue. "Et2Zn-Mediated Rearrangement of Bromohydrins." Journal of Organic Chemistry 73, no. 9 (2008): 3516–22. http://dx.doi.org/10.1021/jo800231s.

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5

Song, Song, Xiaoqiang Huang, Yu-Feng Liang, Conghui Tang, Xinwei Li, and Ning Jiao. "From simple organobromides or olefins to highly value-added bromohydrins: a versatile performance of dimethyl sulfoxide." Green Chemistry 17, no. 5 (2015): 2727–31. http://dx.doi.org/10.1039/c5gc00184f.

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6

Lin, Mei-Huey, Yu-Chun Chen, Shih-Hao Chiu, Kung-Yu Liang, Yi-Lin Lee та Tsung-Hsun Chuang. "Stereoselective preparation of conjugated (Z)-1,3-enynes by dehydration reactions of allenic bromohydrins and the use of the enynes in base-mediated tandem allylation ene-carbocyclization reactions with β-ketoesters". Organic & Biomolecular Chemistry 15, № 3 (2017): 605–9. http://dx.doi.org/10.1039/c6ob02178f.

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7

Li, Jing, and Yian Shi. "Catalytic enantioselective bromohydroxylation of cinnamyl alcohols." RSC Advances 11, no. 22 (2021): 13040–46. http://dx.doi.org/10.1039/d1ra02297k.

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8

Sharghi, Hashem, and Hossein Naeimi. "Metalloporphyrins as New Catalysts in the Highly Regioselective Conversion of Epoxides to Halohydrins with Molecular Halogen." Journal of Chemical Research 23, no. 5 (1999): 310–11. http://dx.doi.org/10.1177/174751989902300507.

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9

Crossley, MJ, SR Davies, and TW Hambley. "Studies Directed Towards the Total Synthesis of Anticapsin and Related Compounds. IV. Competitive Reaction of Amino and Carboxy Substituents in the Halohydrination of 2-Aminobicyclo[2.2.2]oct-5-ene-2-carboxylic Acid Derivatives." Australian Journal of Chemistry 47, no. 12 (1994): 2221. http://dx.doi.org/10.1071/ch9942221.

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Bromohydrination of benzyl (1RS,2SR,4SR)-2-benzyloxycarbonylamino-1-trimethylsilyloxy-bicyclo[2.2.2]oct-5-ene-2-carboxylate (6a) and the (1RS,2RS,4SR)- diastereomer (6b) with N- bromoacetamide in aqueous dioxan has been investigated. These reactions are highly regio-and stereo-selective and give the corresponding bromohydrins (9a) and (9b), but in moderate to low yield. These bromohydrins have the necessary stereochemistry for conversion into anticapsin. The other products from the reaction are tricyclic compounds formed by capture of the anti- bromonium cation intermediates or resultant bromo

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10

Piva, Olivier. "Direct conversion of bromohydrins to ketones." Tetrahedron Letters 33, no. 18 (1992): 2459–60. http://dx.doi.org/10.1016/s0040-4039(00)92214-7.

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11

Li, Jing, Zequan Li, Xun Zhang, Bing Xu, and Yian Shi. "Catalytic enantioselective bromohydroxylation of aryl olefins with flexible functionalities." Organic Chemistry Frontiers 4, no. 6 (2017): 1084–90. http://dx.doi.org/10.1039/c6qo00636a.

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A highly enantioselective bromohydroxylation of aryl olefins with flexible functionalities has been achieved with (DHQD)<sub>2</sub>PHAL as a catalyst and H<sub>2</sub>O as a nucleophile, giving a variety of optically active bromohydrins with up to 98% ee.

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12

Villar-Barro, Ángela, Vicente Gotor, and Rosario Brieva. "Enzymatic resolution of five membered heterocyclic bromohydrins." Tetrahedron: Asymmetry 24, no. 11 (2013): 694–98. http://dx.doi.org/10.1016/j.tetasy.2013.04.012.

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13

Dezor-Mazur, Maria, and Krzysztof Golankiewicz. "Mass spectra of bromohydrins of uracil derivatives." Organic Mass Spectrometry 22, no. 4 (1987): 197–202. http://dx.doi.org/10.1002/oms.1210220404.

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14

PIVA, O. "ChemInform Abstract: Direct Conversion of Bromohydrins to Ketones." ChemInform 23, no. 44 (2010): no. http://dx.doi.org/10.1002/chin.199244151.

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15

SHAFIULLAH, SHAMSUZZAMAN, and R.K.PATHAK. "Synthesis of 6B,19-0xido-steroids." Journal of Indian Chemical Society Vol. 67, Sep 1990 (1990): 774–75. https://doi.org/10.5281/zenodo.6257366.

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Steroid Research Laboratory, Department of Chemistry, Aligarh Muslim University, Aligarh-202 002 <em>Manuscript received 28 November 1989, accepted 19 June 1990</em> Synthesis of 6\(\beta\),19-Oxido-steroids

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16

Wang, Zhihui, Meiyi Li, Wenqin Zhang, Jiangnan Jia, Fei Wang, and Song Xue. "CF3CO2ZnEt-mediated highly regioselective rearrangement of bromohydrins to aldehydes." Tetrahedron Letters 52, no. 45 (2011): 5968–71. http://dx.doi.org/10.1016/j.tetlet.2011.08.134.

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17

Buchanan, G. W., J. W. Bovenkamp, A. Rodrigue, R. A. B. Bannard, and R. Y. Moir. "Application of 13C nuclear magnetic resonance to the conformational analysis of vicinally di- and trisubstituted cyclohexanes: halohydrins, methoxyhalohydrins, and their acetates." Canadian Journal of Chemistry 63, no. 8 (1985): 2143–48. http://dx.doi.org/10.1139/v85-353.

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Low temperature 13C nuclear magnetic resonance spectroscopy has been employed to obtain the chemical shifts and to examine the conformational equilibria of the four chlorohydrins and bromohydrins of 3-methoxycyclohexene. The corresponding acetates and the unsubstituted halohydrins have also been examined. The observed chemical shifts were compared with those calculated from additivity considerations. Limitations of this approach are discussed. Relative peak area measurements have been used to obtain conformational free energies in favourable cases.

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18

Shustov, Gennady V., Melanie K. Chandler, and Saul Wolfe. "Stereoselective synthesis of multiply substituted [1,2]oxazinan-3-ones via ring-closing metathesis." Canadian Journal of Chemistry 83, no. 2 (2005): 93–103. http://dx.doi.org/10.1139/v04-174.

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The title compounds are α-amino acids whose nitrogen atoms are enclosed within 4,5-disubstituted, six-membered cyclic hydroxamates and they are of interest as potential β-lactam surrogates. The compounds have been synthesized in the present work by functionalization of the double bonds of N-substituted 6H-[1,2]oxazin-3-ones, which are obtained upon successive reaction of the triflates of S-α-hydroxy esters with O-allylhydroxylamine and acryloyl chloride, followed by cyclization of the resulting R-α-N-acryloyl-N-allyloxyamino esters in the presence of the ring-closing metathesis (RCM) catalyst

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19

Roy, Chandra D., and Herbert C. Brown. "Monobromoborane - Dimethyl Sulfide—a Highly Promising Reagent for the Regio- and Chemoselective Brominative Cleavage of Terminal Epoxides into Vicinal Bromohydrins." Australian Journal of Chemistry 60, no. 2 (2007): 139. http://dx.doi.org/10.1071/ch06408.

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Monobromoborane–dimethyl sulfide (BH2Br–SMe2) is a highly regio- and chemoselective reagent useful for the brominative cleavage of the epoxy moiety into bromohydrins in the presence of alkenes, alkynes, ethers, acetals, ketals, and acetonides at 0°C, besides being an excellent hydroborating reagent. Several reactive functional groups, such as chloride, ketones, esters, nitriles, nitros, and thioethers, have been accommodated during such transformations. Although the reduction of acetophenone was completely suppressed at –25°C, 4-chlorobenzaldehyde still underwent 12–13% reduction of an aldehyd

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20

Giomi, Donatella, Antonella Salvini, Jacopo Ceccarelli, and Alberto Brandi. "Bromotrimethylsilane as a selective reagent for the synthesis of bromohydrins." RSC Advances 11, no. 24 (2021): 14453–58. http://dx.doi.org/10.1039/d1ra01980e.

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Glycerol, a by-product of biodiesel production, can be efficiently converted into α-monobromohydrin or α,γ-dibromohydrin with trimethylsilyl bromide (TMSBr), in solvent-free and mild reaction conditions.

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21

Takeichi, Tsutomu, Teruo Takakura, Michihiro Ishimori, and Teiji Tsuruta. "Catalytic Asymmetric Cyclization of Some Bromohydrins with Chiral Cobalt Complex." Bulletin of the Chemical Society of Japan 61, no. 2 (1988): 603–5. http://dx.doi.org/10.1246/bcsj.61.603.

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22

Bell, Thonas W., and James A. Ciaccio. "Conversion of epoxides to bromohydrins by B-bromobis (dimethylamino) borane." Tetrahedron Letters 27, no. 7 (1986): 827–30. http://dx.doi.org/10.1016/s0040-4039(00)84111-8.

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23

Douki, Thierry, Guillaume Vadesne-Bauer, and Jean Cadet. "Formation of a Methide Derivative upon Photolysis of Thymidine Bromohydrins." Journal of Organic Chemistry 68, no. 2 (2003): 478–82. http://dx.doi.org/10.1021/jo026606i.

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24

Carr, Anitra C., Christine C. Winterbourn, and Jeroen J. M. van den Berg. "Peroxidase-Mediated Bromination of Unsaturated Fatty Acids to Form Bromohydrins." Archives of Biochemistry and Biophysics 327, no. 2 (1996): 227–33. http://dx.doi.org/10.1006/abbi.1996.0114.

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25

Hartung, Jens, Yvonne Dumont, Marco Greb, et al. "On the reactivity of bromoperoxidase I (Ascophyllum nodosum) in buffered organic media: Formation of carbon bromine bonds." Pure and Applied Chemistry 81, no. 7 (2009): 1251–64. http://dx.doi.org/10.1351/pac-con-08-09-01.

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Peroxidase (PO) activity of vanadate(V)-dependent bromoperoxidase (BPO) I (Ascophyllum nodosum) [VBrPO(AnI)] was retained with a half-life time of ~60 days, if stored in H2O2-incubated, morpholin-4-ethane sulfonic acid (MES)-buffered aqueous alcoholic solutions. These conditions were applied for converting bromide and, e.g., methyl pyrrole-2-carboxylate into bromopyrroles with an almost quantitative peroxide yield. δ,&epsilon;-unsaturated alcohols furnished β-bromohydrins and products of bromocyclization, i.e., tetrahydrofurans and tetrahydropyrans (70–84 % mass balance), if treated with H

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26

Vissers, M. C. M., A. C. Carr, and C. C. Winterbourn. "Fatty acid chlorohydrins and bromohydrins are cytotoxic to human endothelial cells." Redox Report 6, no. 1 (2001): 49–56. http://dx.doi.org/10.1179/135100001101536030.

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27

Panasenko, O. M., H. Spalteholz, J. Schiller, and J. Arnhold. "Leukocytic myeloperoxidase-mediated formation of bromohydrins and lysophospholipids from unsaturated phosphatidylcholines." Biochemistry (Moscow) 71, no. 5 (2006): 571–80. http://dx.doi.org/10.1134/s0006297906050178.

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28

Pappula, Venkatanarayana, Ramachandra Reddy Donthiri, Chandra Mohan Darapaneni та Adimurthy Subbarayappa. "H-β-zeolite catalyzed synthesis of β-bromostyrenes from styrene bromohydrins". Tetrahedron Letters 55, № 10 (2014): 1793–95. http://dx.doi.org/10.1016/j.tetlet.2014.01.118.

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29

YONEDA, F., T. AKIYAMA, M. OHNO, R. YANADA, and T. HARAYAMA. "ChemInform Abstract: The Repair of Thymidine Phosphate Bromohydrins, Oxidatively Damaged Nucleotides." ChemInform 22, no. 12 (2010): no. http://dx.doi.org/10.1002/chin.199112334.

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30

Wang, Zhihui, Meiyi Li, Wenqin Zhang, Jiangnan Jia, Fei Wang, and Song Xue. "ChemInform Abstract: CF3Co2ZnEt-Mediated Highly Regioselective Rearrangement of Bromohydrins to Aldehydes." ChemInform 43, no. 9 (2012): no. http://dx.doi.org/10.1002/chin.201209071.

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31

Ciaccio, James A., Elizabeth Heller, and Adrian Talbot. "Regio- and Chemoselective Ring Opening of Epoxides to Bromohydrins with Dilithium Tetrabromocuprate." Synlett 1991, no. 04 (1991): 248–50. http://dx.doi.org/10.1055/s-1991-20695.

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32

Lin, Mei-Huey, Yi-Syuan Li, Chung-Kai Kuo, et al. "Synthesis of Hexahydro-1H-isoindole Derivatives from Arylacyl Bromides via Homoallenic Bromohydrins." Journal of Organic Chemistry 80, no. 4 (2015): 2462–66. http://dx.doi.org/10.1021/acs.joc.5b00072.

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33

Boyes, Scott A., та Alan T. Hewson. "Enantioselective synthesis of α-bromo acid derivatives and bromohydrins † from tartrate derived bromoacetals". Journal of the Chemical Society, Perkin Transactions 1, № 16 (2000): 2759–65. http://dx.doi.org/10.1039/b002106g.

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34

Santhosh, K. C., and K. K. Balasubramanian. "A Facile and Stereoselective Synthesis of Arylethers of Vicinal Bromohydrins by Mitsunobu Reaction." Synthetic Communications 24, no. 8 (1994): 1049–56. http://dx.doi.org/10.1080/00397919408011698.

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35

Firdoussi, Larbi, Saadia Oubaassine, Brahim Boualy, Soufiane Houssame, and Mustapha Ali. "One-Pot Transformation of Olefins into -Aminoalcohols Via Vic-Bromohydrins Catalyzed by Silica." Journal of Advanced Catalysis Science and Technology 1, no. 2 (2014): 10–15. http://dx.doi.org/10.15379/2408-9834.2014.01.02.02.

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36

Bhuvaneswari, N., K. K. Balasubramanian, and C. S. Venkatachalam. "Proton-transfer reactions in the cathodic reduction of bromohydrins in neutral aprotic media." Journal of Electroanalytical Chemistry 354, no. 1-2 (1993): 223–30. http://dx.doi.org/10.1016/0022-0728(93)80335-f.

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37

Pappula, Venkatanarayana, Ramachandra Reddy Donthiri, Darapaneni Chandra Mohan та Subbarayappa Adimurthy. "ChemInform Abstract: H-β-Zeolite Catalyzed Synthesis of β-Bromostyrenes from Styrene Bromohydrins." ChemInform 45, № 33 (2014): no. http://dx.doi.org/10.1002/chin.201433070.

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38

Lodh, Raj Sekhar, Arun Jyoti Borah, and Prodeep Phukan. "ChemInform Abstract: Synthesis of Bromohydrins Using NBS in Presence of Iodine as Catalyst." ChemInform 46, no. 19 (2015): no. http://dx.doi.org/10.1002/chin.201519093.

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39

Wrigstedt, Pauli, Vladimir Iashin, Kalle Lagerblom, Juha Keskiväli, Konstantin Chernichenko, and Timo Repo. "Syntheses of C-6 Aryl- and Alkynyl-Substituted Thymidines from Thymidinetrans-5,6-Bromohydrins." European Journal of Organic Chemistry 2017, no. 4 (2017): 880–91. http://dx.doi.org/10.1002/ejoc.201601219.

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40

Cao, Yi-Ming, Dieter Lentz, and Mathias Christmann. "Synthesis of Enantioenriched Bromohydrins via Divergent Reactions of Racemic Intermediates from Anchimeric Oxygen Borrowing." Journal of the American Chemical Society 140, no. 34 (2018): 10677–81. http://dx.doi.org/10.1021/jacs.8b06432.

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41

Lang, Fengrui, Darren J. Kassab, and Bruce Ganem. "Neighboring group effects in the regioselective cyclization of vicinal trans-1,2-bromohydrins to epoxides." Tetrahedron Letters 39, no. 33 (1998): 5903–6. http://dx.doi.org/10.1016/s0040-4039(98)01243-x.

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42

Kaur, Kirandeep, Swapandeep Singh Chimni, Harvinder Singh Saini та Bhupinder Singh Chadha. "Pseudomonas gessardii growing cells as a new biocatalyst for asymmetric synthesis of α-bromohydrins". Biocatalysis and Agricultural Biotechnology 4, № 1 (2015): 49–54. http://dx.doi.org/10.1016/j.bcab.2014.10.004.

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43

Dolenc, Darko, and Maja Harej. "Direct Conversion of Bromohydrins to Ketones by a Free Radical Elimination of Hydrogen Bromide1." Journal of Organic Chemistry 67, no. 1 (2002): 312–13. http://dx.doi.org/10.1021/jo016113y.

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44

Lin, Mei-Huey, Yi-Syuan Li, Chung-Kai Kuo, et al. "ChemInform Abstract: Synthesis of Hexahydro-1H-isoindole Derivatives from Arylacyl Bromides via Homoallenic Bromohydrins." ChemInform 46, no. 28 (2015): no. http://dx.doi.org/10.1002/chin.201528152.

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45

CIACCIO, J. A., E. HELLER, and A. TALBOR. "ChemInform Abstract: Regio- and Chemoselective Ring Opening of Epoxides to Bromohydrins with Dilithium Tetrabromocuprate." ChemInform 23, no. 1 (2010): no. http://dx.doi.org/10.1002/chin.199201087.

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46

Bityukov, Oleg V., Vera A. Vil', Gennady I. Nikishin, and Alexander O. Terent'ev. "Alkene, Bromide, and ROH – How To Achieve Selectivity? Electrochemical Synthesis of Bromohydrins and Their Ethers." Advanced Synthesis & Catalysis 363, no. 12 (2021): 3070–78. http://dx.doi.org/10.1002/adsc.202100161.

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47

Lin, Mei-Huey, Chung-Kai Kuo, Wei-Cheng Lin, et al. "Formation of homoallylic bromohydrins in indium-mediated allylation reactions of phenacyl bromides in aqueous solution." Tetrahedron 69, no. 38 (2013): 8263–68. http://dx.doi.org/10.1016/j.tet.2013.07.012.

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48

Cavanagh, Joseph E., Howard S. Weinberg, Avram Gold, et al. "Ozonation byproducts: identification of bromohydrins from the ozonation of natural waters with enhanced bromide levels." Environmental Science & Technology 26, no. 8 (1992): 1658–62. http://dx.doi.org/10.1021/es00032a027.

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49

Takeichi, Tsutomu, Yoshiyuki Ozaki, and Yuzi Takayama. "Asymmetric Carbon Dioxide Fixation into Optically Active Propylene Carbonate by the Reactions of Propylene Bromohydrins." Chemistry Letters 16, no. 6 (1987): 1137–40. http://dx.doi.org/10.1246/cl.1987.1137.

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50

Boyes, Scott A., та Alan T. Hewson. "ChemInform Abstract: Enantioselective Synthesis of α-Bromo Acid Derivatives and Bromohydrins from Tartrate Derived Bromoacetals." ChemInform 31, № 51 (2000): no. http://dx.doi.org/10.1002/chin.200051029.

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