Tetrahedron

Electrophile-initiated selective ring transformations of cyclopropyl ketones

M Demuth, G Mikhail

Index: Demuth, Martin; Mikhail, Gamal Tetrahedron, 1983 , vol. 39, # 6 p. 991 - 997

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Citation Number: 28

Abstract

Electrophile-mediated cyclopropane cleavage in tricyclo [3.3. 0.02, 8] octan-3-one (1a) is increasingly directed towards the maximum bond overlap site in the following order of reagents: acetyl methanesulfonate,+ Br-or I-; t-butyl-dimethylsilyl iodide; t-butyldimethylsilyl trifluoroacetate; trimethylsilyl trifluoroacetate. The latter reagent gives rise to one single regioisomer (→ 6a). Routine yields of isolated products lie between 78 and 87%. ...

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