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Einige Reaktionen des 8,8-Dibromtetracyclo2,4.03,5>octans
Christl, Manfred,Lechner, Monika
, p. 1 - 13 (2007/10/02)
The title compound 2, easily prepared by addition of dibromocarbene to homobenzvalene (7), forms 5-ethinyl-1,3-cyclohexadiene (9) on treatment with methyllithium.Its structure was proved through the additions to 4-phenyl-1,2,4-triazolinedione and 2,3,5,6-tetramethylbenzonitrile oxide, leading to 10 and 12 respectively. 2H and 12C labeled 2 were used to determine the reorganization of the carbon atoms.The results support the proposed reaction mechanism.On heating of 2 the dibromocyclopropane moiety remains intact and dibromo-trans-bishomobenzene (20) is formed, with boron trifluoride-ether 2 rearranges to 20 already at room temperature.Sodium in liquid ammonia debrominates 2 as well as 20 to produce the known parent hydrocarbons 8 and 21 respectively.
