Generation and chemical properties of dicyclopropylcarbene. Ring expansion, chlorine abstraction, carbon-hydrogen bond insertion, and alkene addition reactions

…, PA Risbood, J Warkentin

Index: Bekhazi, Michel; Risbood, Prabhakar A.; Warkentin, John Journal of the American Chemical Society, 1983 , vol. 105, # 17 p. 5675 - 5679

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Citation Number: 11

Abstract

Abstract: Thermolysis of 5, 5-dicyclopropyl-2-methoxy-2-methyl-~ 3-1, 3, 4-oxadiazoline in solution at 80" C affords dicyclopropylcarbene and methyl acetate in high yields. Dicyclopropylcarbene undergoes a variety of reactions including ring expansion to I- cyclopropylcyclobutene, chlorine atom abstraction from carbon tetrachloride, and efficient insertion into the CH bond of chloroform. A rationale for the very different reactions of the ...