Bulletin of the Chemical Society of Japan

Studies of Thioiminocarbonates. I. The Formation and Decomposition of O-Alkyl S-Aryl Thioiminocarbonates in the Reaction of Aryl Thiocyanates with Alcohols in the …

K Tanaka, J Hayami, A Kaji

Index: Tanaka,K. et al. Bulletin of the Chemical Society of Japan, 1971 , vol. 44, p. 2815 - 2820

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Citation Number: 8

Abstract

The reactions of aryl thiocyanates (I) with alcohol in the presence of cyanide ion were found to give alkyl aryl sulfides (III). The intermediate was isolated in the case of p-tolyl thiocyanate with methanol at 0° C and was determined to be O-methyl Sp-tolyl thioiminocarbonate (IIa) on the basis of NMR and IR spectral studies. The treatment of IIa with the cyanide ion afforded methyl p-tolyl sulfide (IIIa) in a high yield. When a mixture of an equimolecular ...