140137-89-9Relevant articles and documents
Difluoromethyl and chlorofluoromethyl sulfoximines: Synthesis and evaluation as electrophilic perfluoroalkylating reagents
Pégot, Bruce,Urban, Céline,Bourne, Aaron,Le, Thanh Nghi,Bouvet, Sébastien,Marrot, Jér?me,Diter, Patrick,Magnier, Emmanuel
, p. 3069 - 3075 (2015/05/13)
An efficient and convenient method is described that allows the synthesis of a set of difluoromethyl sulfoximines, as well as chlorofluoromethyl sulfoxides, sulfones, and sulfoximines. Our procedure does not require metals or nonrecommended freons, and it gives rise to an original route to Hu's reagent. Unprecedented chlorofluoromethyl sulfoximines have been also isolated, and these compounds have been shown to act as an electrophilic source of this original bis-halogenated moiety. The mechanism of the electrophilic chlorofluoromethylation is also discussed. Bromodifluoromethyl and dichlorofluoromethyl sulfoximines are transformed into the Hu electrophilic difluoromethylating reagent, and into a new chlorofluoromethylating reagent, respectively.
Behaviors of α-Fluorocarbenoids Derived from the Nucleophilic Desulfinylation of α-Chloro-α-fluoroalkyl Sulfoxides
Uno, Hidemitsu,Sakamoto, Katsuji,Semba, Fumihiko,Suzuki, Hitomi
, p. 210 - 217 (2007/10/02)
2-Aryl-1-chloro-1-fluoroethyl sulfoxides underwent nucleophilic desulfinylation with PhMgBr to give (Z)-fluorostyrene derivatives in a very stereoselective manner (>33:1) via an α-fluorocarbene species.When treated with 3 equiv of PhLi in the presence of N,N,N',N'-tetramethylethylenediamine, they similarly formed fluorostyrenes as a stereoisomeric mixture (E:Z = 2:1), but with 1 equiv of PhLi 1-aryl-1-chloro-1-fluoroethanes were the major product.On the other hand, no formation of a fluoroalkene was observed in the desulfinylation of 1-chloro-1-fluoro-4-phenylbutyl sul foxide with the nucleophiles.In the latter reaction, oxidation and/or phenylation of the intermediate carbene were the main pathways.