The Journal of organic chemistry

Studies on the Thermal Ring-Opening Reactions of cis-3, 4-Bis (organosilyl) cyclobutenes

M Hasegawa, M Murakami

Index: Hasegawa, Munehiro; Murakami, Masahiro Journal of Organic Chemistry, 2007 , vol. 72, # 10 p. 3764 - 3769

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Citation Number: 24

Abstract

Three cis-3, 4-bis (organosilyl) cyclobutenes were synthesized, and their thermal ring- opening reactions were studied. The ring-opening reaction of cis-3, 4-bis (trimethylsilyl) cyclobutene proceeded remarkably faster than that of cis-3, 4-dimethylcyclobutene. The significant rate acceleration was explained by assuming (i) stabilization of the transition state by electron delocalization from the cyclobutene HOMO to the Si-CH3 σ* orbital,(ii) ...