7133-40-6Relevant articles and documents
Aliphatic thioethers by s-alkylation of thiols via trialkyl borates
Gunes, Deniz,Sirkecioglu, Okan,Bicak, Niyazi
experimental part, p. 1685 - 1690 (2010/09/17)
A simple and convenient one-pot procedure is described for the synthesis of thioethers via boron esters. This procedure involves in-situ generation of alkyl sulfates by reaction of trialkyl borates with concentrated sulfuric acid and subsequent reaction with thiols in the presence of pyridine. The reactions with boron esters of primary or secondary alcohols proceed cleanly at 100C and afford aliphatic thioethers in reasonable yields (59-93%) within 24 h. Interestingly, the 1H NMR spectra of the products showed no sign of positional isomerisms. The method fails however with thiophenol and does not yield aromatic thioethers, due to electrophilic substitution at the phenyl ring. Copyright Taylor & Francis Group, LLC.
Biotransformation of organic sulfides - VIII. A predictive model for sulfoxidation by Helminthosporium species NRRL 4671
Holland, Herbert L.,Brown, Frances M.,Lakshmaiah, Gingipalli,Larsen, Brett G.,Patel, Manish
, p. 683 - 697 (2007/10/03)
The fungus Helminthosporium species NRRL 4671 converts a wide range of prochiral sulfides to the corresponding chiral sulfoxides, the majority of which have (S) configuration at sulfur. The formation of a series of chiral cyclopentyl alkyl, cyclohexyl alkyl, benzyl alkyl, and methyl alkyl sulfoxides by biotransformation of the corresponding sulfides using Helminthosporium species is described. The analysis of over 90 such biotransformations has resulted in the development of a model based on restrictive-space descriptors that has been used to rationalize these reactions, and that is proposed as a predictor of the outcome of Helminthosporium-catalyzed sulfoxidations.
