The Journal of Organic Chemistry

Improved selectivity in the preparation of some 1, 1-difunctionalized 3-cyclopentenes. High yield synthesis of 3-cyclopentenecarboxylic acid

JP Depres, AE Greene

Index: Depres, Jean-Pierre; Greene, Andrew E. Journal of Organic Chemistry, 1984 , vol. 49, # 5 p. 928 - 931

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Citation Number: 58

Abstract

yield is only 16%. 2b Schmid and Wolkoffz" have reported the selective obtention of 2b by the rearrangement at 400-425" C of the vinylcyclopropane derivative 4b, secured from diethyl malonate and trans-1, 4-dichloro-2-butene, and the conversion of 2b as before to acid 3 (32% overall yield). Alternatively, 3 has been prepared from cyclopentadiene in five steps in 19% overall yield.'j Recently, we required large amounts of acid 3 for work on a ...