Tetrahedron p. 2429 - 2434 (1982)
Update date:2022-08-03
Topics:
Nagendrappa, Gopalpur
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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Doi:10.1002/jhet.5570190657
(1982)Doi:10.1055/s-2005-862389
(2005)Doi:10.1002/adsc.201500711
(2015)Doi:10.1007/BF00512807
(1983)Doi:10.1016/j.bmcl.2005.05.017
(2005)Doi:10.1039/c5sc03761a
(2016)
