Chemoselective reaction of a sulfonate ester with methoxide ions in preference to benzyl mercaptide anions
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.
Langler, Richard Francis,Morrison, Nancy Ann
p. 2385 - 2389
(2007/10/02)
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