Ring-Opening and Ring Expansion Study of 3, 4-Di (1-adamantyl)-1, 2-dithiete.

J Nakayama, N Masui, Y Sugihara, A Ishii

Index: Nakayama, Juzo; Masui, Nobuo; Sugihara, Yoshiaki; Ishii, Akihiko Bulletin of the Chemical Society of Japan, 1998 , vol. 71, # 5 p. 1181 - 1186

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Citation Number: 19

Abstract

Reduction of 3, 4-di (1-adamantyl)-1, 2-dithiete (2) with LiEt 3 BH, followed by treatment with MeI, gave (E)-1, 2-di (1-adamantyl)-1, 2-bis (methylthio) ethene (7-E) in 87% yield. Configuration of the double bond part of 7-E was determined by X-ray diffraction analysis. Treatment of 2 with MeLi and then with MeI also gave the same alkene 7-E in 90% yield, whereas treatment of 2 with MeLi followed by acidification afforded thermally labile (E)-1, ...