89841-23-6Relevant academic research and scientific papers
Olefination with Sulfonyl Halides and Esters: Scope, Limitations, and Mechanistic Studies of the Hawkins Reaction
Górski, Bartosz,Talko, Alicja,Basak, Tymoteusz,Barbasiewicz, Micha?
supporting information, p. 1756 - 1759 (2017/04/11)
Carbanions of alkanesulfonyl halides and esters react with nonenolizable carbonyl compounds to give olefins. Mechanistic studies reveal that initial aldol-type addition of the carbanions is followed by cyclization-fragmentation to alkenes, and the leaving group on the sulfonyl moiety (RSO2X) controls carbanion stability and rate of the olefin formation.
Synthesis of sulfonic acid derivatives by oxidative deprotection of thiols using tert-butyl hypochlorite
Joyard, Yoann,Papamicael, Cyril,Bohn, Pierre,Bischoff, Laurent
supporting information, p. 2294 - 2297 (2013/06/05)
Starting from alkyl halides or Michael acceptors, thioacetates were prepared in situ and further treated with t-BuOCl, affording the corresponding sulfonyl chlorides which were trapped with nucleophiles such as water, alcohol, or amines. The three steps can be achieved in a one-pot procedure. Oxidative deprotection also proved to be efficient with S-trityl and S-tert-butyl groups, making it a convenient route toward cysteic acid derivatives.
