Journal of the Chemical Society. Perkin transactions I p. 1934 - 1941 (1981)
Update date:2022-08-02
Topics:
Davis, Anthony P.
Hughes, Gwyneth J.
Lowndes, Peter R.
Robbins, Catherine M.
Thomas, Elizabeth J.
Whitham, Gordon H.
Epoxide ring-opening of 1,2-epoxy-1-trimethylsilylcyclohexane (3) has given a range of the 2-substituted 2-trimethylsilylcyclohexanols (4; X = H, OH, OMe, OCH2CH=CH2, Br, I, SCN) in which attack by nucleophile has occured at the carbon α to silicon.The products (4) have been transformed into a number of functionalised silanes, including the silyl-episulphide (9).Other epoxides which have been less extensively studied are the conformationally biased epoxysilanes (10) and (11), the eight-membered ring epoxysilanes (17) and (21) and the two stereoisomeric 2,3-epoxy-3-trimethylsilylpentanes (26) and (29).Epoxide ring-opening adducts were obtained after treatment with H+-MeOH in all cases except for compound (17), where the bicyclic alcohol (18) was formed by a transannular reaction.
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Doi:10.1039/P19810002604
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