Direct Synthesis of 2, 2-diaryl-3-methyl-2, 3-dihydrobenzothiazoles from 3-methyl-2, 3-dihydrobenzothiazole-2-thione and some mechanistic aspects

KY Akiba, H Shiraishi, N Inamoto

Index: Akiba,K. et al. Bulletin of the Chemical Society of Japan, 1979 , vol. 52, p. 156 - 159

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Citation Number: 33

Abstract

Reactions of 3-methyl-2, 3-dihydrobenzothiazole-2-thione (1) and 3-methyl-2-(methylthio) benzothiazoliumiodide with Grignard reagents gave 2, 2-disubstituted 3-methyl-2, 3- dihydrobenzothiazole (2) as a major product as well as 2, 2′-disubstituted 3, 3′-dimethyl- 2, 2′, 3, 3′-tetrahydrobi (2-benzothiazolyl)(3). Reactions of 1 with organolithiums gave 2 as a major product. The results demonstrate that the formation of 3 is due to the presence ...