Abstract
The acid-catalysed reactions of medium ring α,β-epoxysilane 1 are described. The epoxide 1 gives exclusively the bicyclic alcohol 2 with boron trifluoride etherate. With aqueous sulphuric acid the products are due to both transannular ring closure, 2, and transannular hydride migration, 3 and 4. trans-Cyclooctene derivatives 3 and 4 are formed by the trans-elimination of trimethylsilanol from the likely intermediate β-hydroxysilanes 10 and 11. The results with methanolic sulphuric acid are similar. It is also noticed that the hydride migration is facilitated by the nucleophilic strength of the medium.
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