91551-38-1Relevant articles and documents
SYNTHESIS AND THERMAL TRANSFORMATIONS OF BICYCLOALKENES CONTAINING A METHYLENECYCLOPROPANE FRAGMENT
Mil'vitskaya, E. M.,Pekhk, T. I.,Pereslegina, N. S.,Tarakanova, A. V.,Ivanov, A. V.
, p. 1573 - 1583 (2007/10/02)
The previously undescribed 8-methylenebicyclooct-2-ene (II) and 9-methylenebicyclonon-4-ene (IV) were synthesized by the dehydrohalogenation of 8-methyl-8-chlorobicyclooct-2-ene and 9-methyl-9-chlorobicyclonon-4-ene.It was established that the hydrocarbon (II) is thermally labile, whereas the hydrocarbon (IV) does not change right up to 300 deg C.The thermal transformations of the hydrocarbon (II) and its isomeric bicyclonona-1,6-diene (III) at 100 - 180 deg C were investigated.At 100 deg C a pseudoequilibrium is established between these hydrocarbons.The final and only products from the transformations of both hydrocarbons at 180 deg C are the previously unknown anti-Bredt hydrocarbon bicyclonona-2,7-diene (XXVIIIb) and 3-methylene-1,4-cyclooctadiene (XXV), formed in a ratio of 1 : 2.5.