111128-36-0Relevant articles and documents
Chemoselective reaction of a sulfonate ester with methoxide ions in preference to benzyl mercaptide anions
Langler, Richard Francis,Morrison, Nancy Ann
, p. 2385 - 2389 (2007/10/02)
Trifluoroethyl benzyl sulfide was prepared (in 2-propanol) and subsequently chlorinated as a further test of substituent electronegativity based regiochemical predictions.The initial attempt to prepare that sulfide by reaction of 2,2,2-trifluoroethyl methanesulfonate and benzyl mercaptide anions (in methanol) furnished benzyl methyl sulfide.Mechanistic possibilities are discussed in detail and some synthetic consequences of this novel reaction are presented.