54697-52-8Relevant articles and documents
Episulfone substitution and ring-opening reactions via α-sulfonyl carbanion intermediates
Dishington, Allan P.,Douthwaite, Richard E.,Mortlock, Andrew,Muccioli, Adriano B.,Simpkins, Nigel S.
, p. 323 - 337 (2007/10/03)
Three-membered cyclic sulfones undergo substitution on treatment with base-electrophile mixtures, such as LDA-Me3SiCl and Bu′-P4 phosphazene base-PhCHO, to give either substituted episulfones or the corresponding alkenes following loss of SO2. The structure of a trisilylated episulfone product, 2a, was determined by X-ray crystallography. In the absence of Me3SiCl, reaction of episulfones with lithium diisopropylamide results in ring-opening to give alkenyl sulfinate intermediates, which can be alkylated to give (E)-alkenyl sulfone products in stereoselective fashion.
