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Original Articles

BASE-PROMOTED REARRANGEMENT OF EPOXIDES IN THE 2- AND 3-PHOSPHABICYCLO[3.3.0]HEPTANE SYSTEMS1

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Pages 195-203 | Received 08 Nov 1982, Accepted 04 Jan 1983, Published online: 13 Dec 2006
 

Abstract

Unsaturated alcohols were formed by the base-catalyzed rearrangement of epoxides of saturated cyclopentaphosphole derivatives. Reaction of the 3a,6a-epoxide of the cyclopenta[c]phosphole with cyclo-hexylamine gave a mixture of the two possible alcohols. The 3a,6a-epoxide of the cylopenta[b]phosphole at −50° with n-butyllithium gave only the 3a-hydroxy product, with the double bond in the cyclopentane ring (6,6a), but at higher temperatures migration of the double bond to the 5,6-position occurred. All compounds were characterized by 1H, 13C, and 31P NMR spectroscopic measurements.

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