Unexpected Behavior of an α-Tosyloxy Sulfone Compared with an α-Chloro Sulfone in Base-Induced Reactions

DOI: 10.1021/jo01297a052

Source and publish data:

Journal of Organic Chemistry p. 1719 - 1721 (1980)

Update date:2022-08-11

Topics:

Authors:

Meyers, Cal Y.

Hua, Duy H.

Peacock, Nancy J.

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Article abstract of DOI:10.1021/jo01297a052

Unexpectedly, a rate ratio for k_OTs/k_Cl 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.

Full text of DOI:10.1021/jo01297a052

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