The application of intramolecular radical cyclizations of acylsilanes in the regiospecific formation of cyclic silyl enol ethers

CH Huang, SY Chang, NS Wang…

Index: Huang; Chang; Wang; Tsai Journal of Organic Chemistry, 2001 , vol. 66, # 26 p. 8983 - 8991

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Citation Number: 24

Abstract

Acylsilanes with terminal α-stannyl bromide or xanthate functionalities are prepared. α- Stannyl radicals generated from these acylsilanes undergo intramolecular cyclizations to give cyclic silyl enol ethers regiospecifically. The radical processes involve radical cyclization, Brook rearrangement, and β-fragmentation in sequence. A tributylstannyl group serves as the radical leaving group. The newly formed σ-bond and π-bond are located ...