1,3-Migration of phenylthio group in the rearrangement of tertiary cyclopropylmethanols possessing an α-phenylthio group
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The acid catalysed ring opening of tertiary cyclopropylmethanols 1 (R = H, vinyl, Ph), possessing a phenylthio group on the adjacent carbon atom proceeds, regioselectively and homoallylic halides 2 are obtained in 49 - 86% yields. Depending on the structure of 1 (R= Ph, SPh) and the acid used the cyclopropane ring opening follows the 1,3-migration of phenylthio group and the corresponding 1-halo-3-phenylthio-4-pentene derivatives 3 are obtained in 54-76% yields.