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Various dialkoxychloroethylsilyl enol ether derivatives of pinacolone, upon treatment with tributylstannane and AIBN, underwent free-radical cyclizations to yield isolable 2,2-dialkoxy-1-oxa-2-silacyclohexanes. As the bulkiness of the alkoxy groups increased, the selectivity of the reaction for forming cyclized instead of directly reduced acyclic byproducts improved.
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Walkup et al. (1990) studied this question.
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