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A convenient synthesis of (6 R,7 S)-(+)-himachala-9,11-diene, the pheromone of the chrysomelid beetle Phyllotreta striolata is described. The diene is obtained in a single op eration by a spon- taneous "bromination/dehydrobromination" of 2,6,6,9-tetramethylbicyclo(5.4.0)undec-8-ene. The halogenation/dehalogenation sequence proceeds spontaneously in CCl 4, and is less uniform in CH 2Cl 2 and CHCl 3. 1 H NMR experiments carried out in presence of the radical scavenger di- tert -butyl-4-methylphenol suggest an ionic mechanism for this reaction. Theoretical calculations demonstrate that the spontaneous reaction profits f rom the strongly exergonic addition of Br 2 to the double bond and an almost neutral energy differ ence between the starting olefin and the diene pheromone.

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Improved synthesis of the chrysomelid pheromone (6R,7S)-(+)-himachala-9,11-diene via spontaneous bromination and didehydrobromination of 2,6,6,9-tetramethyl-bicyclo[5.4.0]undec-8-ene