82482-00-6Relevant articles and documents
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.
Photolysis of Alkyl Aryl Sulfoxides: α-Cleavage, Hydrogen Abstraction, and Racemization
Guo, Yushen,Jenks, William S.
, p. 857 - 864 (2007/10/03)
The photochemistry of a series of alkyl aryl sulfoxides is described. The initial event of the photolysis process is homolytic cleavage to form sulfinyl/alkyl radical pairs. The radical pair partitions between recombination to starting material, formation of sulfenic esters, disproportionation to an olefin and benzenesulfenic acid, and formation of typical radical escape products. The quantum yield for conversion depends on the structure or the reactivity of the alkyl radical, with the sequence benzyl > tertiary alkyl > secondary alkyl > primary alkyl > (di)aryl. The high racemization efficiency of some aryl primary-alkyl sulfoxides suggests that another nonradical pathway for the photoracemization process may exist. Product analysis does not support any hydrogen abstraction pathways.
