Controlling the outcome of a carbocation-initiated cyclisation

Abstract
The allylsilane, 6,6-dimethoxy-2-(trimethylsilylmethyl)hex-1-ene (2) gives 3-methylenecyclohexyl methyl ether (7) on treatment with tin(IV) chloride, whereas cyclisation of the corresponding compound without the silyl group (1) was known to give five products (5)–(6). The synthesis of the allylsilane (2) is described.

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