Mechanistic studies of the allylic rearrangements of alpha-silyloxy allylic silanes to silyloxy vinylic silanes |
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| Authors: | Kim Angie I Kimmel Kyle L Romero Antonio Smitrovich Jacqueline H Woerpel K A |
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| Affiliation: | Department of Chemistry, University of California, Irvine, California 92696-2025, USA. |
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| Abstract: | Mechanistic evidence suggests that the Lewis acid-promoted allylic rearrangement of alpha-silyloxy allylic silanes proceeds along an ionic reaction pathway involving a contact ion pair. The driving force for this transformation is alleviation of steric congestion at the allylic position of the alpha-silyloxy allylic silane and stabilization of pi cc by hyperconjugation. |
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