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

Jonathan Clayden*, David W. Watson, Mark Chambers

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

37 Citations (Scopus)


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 presence of an anion stabilising group to proceed. β-Silylketones were similarly formed by Brook-retro-Brook rearrangement on warming acylsilanes with a vinyllithium.

Original languageEnglish
Pages (from-to)3195-3203
Number of pages9
Issue number13
Early online date21 Nov 2004
Publication statusPublished - 28 Mar 2005


  • Anion
  • Cyclopropane
  • Organolithium
  • Rearrrangement
  • Silicon


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