Acid-catalyzed hydrolysis of ketene dithioacetals and trithioorthocarboxylates. Effects of. beta.-methyl substitution

T Okuyama, S Kawao, T Fueno

Index: Okuyama, Tadashi; Kawao, Shoji; Fueno, Takayuki Journal of Organic Chemistry, 1984 , vol. 49, p. 85 - 88

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Citation Number: 15

Abstract

Results Hydrolysis of Ketene Dithioacetals 1. Hydrolysis products obtained from the reaction of lb in 80 vol% CH3CN-H20 (0.02 M HC1) were examined by'H NMR spectroscopy. The spectrum was consistent with S-methyl thiopropionate 4b contaminated by a small amount (- 1/6) of trithioorthopropionate 5b. The latter product must come from the reaction of the intermediate carbocation 2b with methanethiol liberated on the formation of 4b. Products ...