Reaction of organoaluminium reagents with cyclopropylmethyl acetates and 2-vinylcyclopropane-1, 1-dicarboxylate esters.

T Hiyama, Y Morizawa, H Yamamoto…

Index: Hiyama, Tamejiro; Morizawa, Yoshitomi; Yamamoto, Hajime; Nozaki, Hitosi Bulletin of the Chemical Society of Japan, 1981 , vol. 54, # 7 p. 2151 - 2160

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Citation Number: 22

Abstract

Ring-opening alkylation of cyclopropylmethyl acetates was studied. The acetoxyl group of 7- (1-acetoxyheptyl) norcarane is substituted by the alkyl group upon treatment with trialkylaluminium, but alkylation of trans-1-(1-acetoxyethyl)-2-phenylcyclopropane with trialkylaluminium gives rise to trans-5-phenyl-2-alkenes. The reaction of (1S, 2S)-2- phenylcyclopropylmethyl acetate with trimethylaluminium resulted in the complete loss of ...