Journal of Organic Chemistry p. 1719 - 1721 (1980)
Update date:2022-08-11
Topics:
Meyers, Cal Y.
Hua, Duy H.
Peacock, Nancy J.
Unexpectedly, a rate ratio for kOTs/kCl of 0.0011 was observed in 1,3-eliminations of (tosyloxy)methyl benzyl sulfone and chloromethyl benzyl sulfone in t-BuOK/t-BuOH (25 deg C), while in MeONa/MeOH (25 deg C) neither 1,3-elimination occurred; instead, the α-tosyloxy sulfone underwent facile S-O cleavage to provide methyl p-toluenesulfonate and α-toluenesulfinic acid.
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