Can relief of ring-strain in a cyclopropylmethyllithium drive the Brook rearrangement?

J Clayden, DW Watson, M Chambers

Index: Clayden, Jonathan; Watson, David W.; Chambers, Mark Tetrahedron, 2005 , vol. 61, # 13 p. 3195 - 3203

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Citation Number: 28

Abstract

α-Cyclopropyl-α-trialkylsilyl alkoxides were formed either by addition of cyclopropyllithiums to acylsilanes or by addition of organolithiums to a cyclopropylformylsilane.[1, 2]-Brook rearrangement led to α-silyloxy organolithiums which on warming underwent cyclopropane ring opening and [1, 5]-retro-Brook rearrangement to yield γ-silyl ketones. Despite the favourability of the cyclopropane ring opening, the Brook rearrangement still required the ...