Tetrahedron

Reactions of carbenes with bicyclobutanes and quadricyclane: Cycloadditions with two σ bonds

JE Jackson, GB Mock, ML Tetef, G Zheng, M Jones

Index: Jackson, James E.; Mock, George B.; Tetef, Merry L.; Zheng, Guo-Xiu; Jones, Maitland Jr. Tetrahedron, 1985 , vol. 41, # 8 p. 1453 - 1464

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Citation Number: 27

Abstract

Dicarbomethoxycarbene and dichlorocarbene add to 1, 2, 2-trimethylbicyclo [1.1. 0] butanc in such a fashion as to suggest a concerted addition in which the central and side bonds are cleaved simultaneously. MNDO calculations support such a pathway and suggest that endo attack on the bicyclobutane is preferred to exo. Reaction of the same two carbenes with quadricyclane gives substituted derivatives of the exo-tricyclo [3.2. 1.02, 4] oct-6-ene ...