A novel competition between C–Se and C–Si cleavages in cyclization of β-seleno-β-silyl-substituted divinyl ketones
- 1 January 1991
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 6,p. 1555-1560
- https://doi.org/10.1039/p19910001555
Abstract
Reactions of β-seleno-β-silyl-substituted divinyl ketones 2–4 with Lewis acids at room temp. gave phenylseleno and/or trimethylsilyl functionalized cyclopentenones. The use of TiCl4 or SnCl4 results in C–Se cleavage leading to 5-(phenylseleno)-3-(trimethylsilyl)cyclopent-2-enones 9–11 as major products. In contrast, using AgBF4–TMSCI (trimethylsilyl chloride) results in C–Si cleavage to give 3-(phenylseleno)cyclopenten-2-ones 12–14. Lewis acid-dependent competitive cleavage between C–Se and C–Si bonds has been demonstrated.Keywords
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