3-Methylenetricyclo[3.1.0.02,6]hexane, a Tricyclic Isomer of Toluene: Synthesis and Addition onto Tetracyanoethylene

Abstract

A multistep ring-contraction route starting from tricyclo[4.1.0.0 2,7 ]heptan-3-one (1) resulted in a mixture of the title compound 7 and the homofulvene 8 in a ratio of 1:2.5. In a second synthesis, a 3.5:1 mixture of 7 and three additional hydrocarbons was obtained from 4-(phenylsulfanyl)tricyclo[3.1.0.0 2,6 ]hexan-3-one (9) in a two-step sequence. On be-