Abstract
The 1-phenylselenocyclopropylmethyl cations are generated by the reaction of the corresponding cyclopropylmethanols 1 with TsOH. The reaction in methanol proceeds to afford the homoallylic ethers 2, ring-enlargement products 3, 4, and ring opening products 5 depending upon the kind of substituent on the cyclopropane ring or the α-carbon. On the other hand, in the case of the absence of methanol as nucleophile, 4 H-selenochromene derivative 7 is obtained exclusively. The oxidative elimination of the phenylselenyl group in the resulting phenylselenohomoallylic compounds 2 furnishes functionalized allene derivatives and alkyne derivatives.
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