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Synlett 1992; 1992(1): 85-86
DOI: 10.1055/s-1992-21276
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Isomerization of Alkenyl- and Alkynyltricyclo[4.1.0.02,7]heptanes and Some Related Compounds

Georg Kottirsch* , Günter Szeimies
  • *Institut für Organische Chemie, Universität München, Karlstr. 23, D-8000 München 2, Germany
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Publication Date:
18 September 2002 (online)

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Flash vacuum pyrolysis of bridgehead vinyl- and alkynyl-substituted tricyclo[4.1.0.02,7]heptanes 1 at about 400 °C led to the bicyclo[3.2.0]hept-6-enes 2. In two cases, further cyclization of the vinyl substituents afforded the tricycles 3 (4,7-dimethyl- 2,3,3a,5,6,7b-hexahydro-1H-cyclopenta [3,4]cyclobuta[1,2]-benzene) and 4 (4-methyl-2,3,3a,7b-tetrahydro-1H-cyclopenta-[3,4]cyclobuta[1,2]benzene). The rhodium(I)-catalyzed isomerization of 11 [1,2-bis(tricyclo[4.1.0.02,7]hept-1-yl)ethylene] produced via 13 the pentaene 14 [1,2-bis(6-methylene-1-cyclohexenyl)ethylene], whereas irradiation of 1,7-disubstituted tricyclo[4.1.0.02,7]heptanes 15 gave rise to the formation of 1,6-disubstituted bicyclo[3.2.0]hept-6-enes 16.