A mechanistic study on the reaction of iminothiadiazolines with activated acetylenes: Competitive pathway through hypervalent sulfurane and zwitterion.

Y Yamamoto, T Tsuchiya, M Ochiumi, S Arai…

Index: Yamamoto, Yohsuke; Tsuchiya, Tohru; Ochiumi, Masahide; Arai, Shin-ichi; Inamoto, Naoki; Akiba, Kin-ya Bulletin of the Chemical Society of Japan, 1989 , vol. 62, # 1 p. 211 - 218

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Citation Number: 13

Abstract

The reaction of 3-aryl-5-benzoyl-2-imino-2, 3-dihydro-1, 3, 4-thiadiazoles (6) with dimethyl acetylenedicarboxylate (4b) gave the corresponding thiazole (8) and benzoyl cyanide through sulfurane (B) by 1, 3-dipolar cycloaddition and cis-(9) and trans-vinyl (10) compounds through zwitterion (C) by simple addition. Two types of addition reactions competed each other and the ratio of the two [R= B/C] depended solely on the solvent ...