Evidence for a Stepwise Addition of Carbenes to Strained Double Bonds: Reactions of Dihalocarbenes with Cyclopropenes


  • Carbene Rearrangements, Part 47. Prof. W. M. Jones (University of Florida) and Dr. L. Xu are gratefully acknowledged for helpful discussions. Part 46: J. Weber, U. H. Brinker, Tetrahedron1996, 52, 14641.

  • Dedicated to Professor William von Eggers Doering on the occasin of his 80th birthday


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Zwitterionic species are most likely the intermediates for the formation of 1,1-diohalo-2,3-diarylbutadiens by addition of dihalocarbenes to 1,2-diarylcyclopropenes [Eq. (a)]. Bicyclobutanes can be out as intermediates for the formation of butadienes.