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Issue 10, 1998
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Reactions of β-trimethylstannylcyclohexanones with peracids: investigations into the stannyl-directed Baeyer–Villiger reaction

Abstract

The trimethylstannyl substituent raises the migratory aptitude of a primary β-carbon to be above that of a not otherwise activated secondary or tertiary carbon. This is apparent from the exclusive formation of the alkene acids 9–11 from Baeyer–Villiger reaction of the β-stannyl cyclohexanones 3–5. The stereoelectronic requirements of the stannyl-directed Baeyer–Villiger reaction were investigated using the axial β-trimethylstannylcyclohexanone 20.

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Article information


J. Chem. Soc., Perkin Trans. 2, 1998, 2151-2154
Article type
Paper

Reactions of β-trimethylstannylcyclohexanones with peracids: investigations into the stannyl-directed Baeyer–Villiger reaction

S. Horvat, P. Karallas and J. M. White, J. Chem. Soc., Perkin Trans. 2, 1998, 2151
DOI: 10.1039/A804427I

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