19405-19-7Relevant academic research and scientific papers
3-Methylenetricyclo[3.1.0.02,6]hexane, a tricyclic isomer of toluene: Synthesis and addition onto tetracyanoethylene
Hasselmann, Dieter,Loosen, Klaus,Fischer, Thomas,Kunz, Ulrike,Christl, Manfred
, p. 1374 - 1379 (2002)
A multistep ring-contraction route starting from tricyclo[4.1.0.02,7]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 [3.1.0.02,6]hexan-3-one (9) in a two-step sequence. On being heated at 175 °C in solution, 7 rearranged to toluene. Treatment of 7 with tetracyanoethylene gave rise to a 1:5 mixture of the [2+2] cycloadduct 16 and the cyclopropadicyclopentene derivative 17. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
