Dimerization of cyclopropanecarboxylic acid dianion and thermal decarboxylative rearrangement of the dimer to 2-cyclopropyl-4, 5-dihydrofuran

EGE Jahngen, D Phillips, RJ Kobelski…

Index: Jahngen, Edwin G. E.; Phillips, Douglas; Kobelski, Robert J.; Demko, Donald M. Journal of Organic Chemistry, 1983 , vol. 48, # 15 p. 2472 - 2476

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Citation Number: 9

Abstract

The dianion of cyclopropanecarboxylic acid (2) reacted with alkyl halides and deuterated water at temperatures below 0" C; however, self-condensation to the D-keto acid 3 was the only obrved product at elevated temperatures. This observation contrasts the self- condensation of the ethyl ester where a trimeric diester alcohol is the product. Attempted mixed condensations of the dianion 2 and carboxylic acids without acidic a-protons did ...