67653-36-5Relevant academic research and scientific papers
Pummerer Cyclization Revisited: Unraveling of Acyl Oxonium Ion and Vinyl Sulfide Pathways
Li, Xin,Carter, Rich G.
, p. 5541 - 5545 (2018/09/25)
Two viable pathways (vinyl sulfide and acyl oxonium ion) for the Pummerer cyclization have been unraveled that expand the reaction scope and capabilities. Use of Br?nsted-enhanced Lewis acidity was key to realization of the vinyl sulfide pathway, whereas selective complexation of the sulfur lone pair facilitated the unprecedented acyl oxonium ion pathway. Preliminary mechanistic investigations support these hypotheses. A range of substrates have been explored to understand the reaction parameters.
Sulfoxidation of alkenes and alkynes with NFSI as a radical initiator and selective oxidant
Zhang, Yuexia,Wong, Zeng Rong,Wu, Xingxing,Lauw, Sherman J. L.,Huang, Xuan,Webster, Richard D.,Chi, Yonggui Robin
supporting information, p. 184 - 187 (2016/12/27)
Sulfoxides are important functional molecules. We develop a short-route (one-pot) synthesis of this class of molecules by reacting thiols with alkenes or alkynes under mild and metal-free conditions. N-Fluorobenzenesulfonimide (NFSI) is used to play dual roles: as a radical initiator for a thiol-ene/-yne reaction to form sulfide adducts, and as efficient oxidant for conversion of the sulfides formed in situ to sulfoxides. Over-oxidation of the sulfoxides to sulfones is avoided in our approach.
Stereoselective synthesis of (E)-Vinyl Sulfoxides by the Horner-Wittig reaction
Van Steenis, Jan Hein,Van Es, Joseph Johannes Gerardus Steven,Van Der Gen, Arne
, p. 2787 - 2793 (2007/10/03)
The Horner-Wittig reaction of sulfinylmethyl-substituted di-phenylphosphane oxides 1-3 with aldehydes is reported. In a straightforward synthesis, (E)-vinyl sulfoxides 4 (R1 = Ph), 5 (R1 = Me) and 6 (R1=pTol) were formed m
