51422-66-3Relevant academic research and scientific papers
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.
TRANSFORMATIONS OF HYDROCARBONS OF BICYCLOHEPTANE SERIES WHEN TREATED WITH POTASSIUM tert-BUTOXIDE AND DIMSYL IN DIMETHYL SULFOXIDE
Mil'vitskaya, E. M.,Babushkina, O. Ya.,Ranneva, Yu. I.,Shapiro, I. O.,Luzikov, Yu. N.,et al.
, p. 1243 - 1246 (2007/10/02)
Bicycloheptane when treated with potassium tert-butoxide and dimsyl in DMSO remains unchanged.Its unsaturated derivatives in these solutions isomerize either with opening of the small ring or with a shift of the double bond in the six-membered ring.In the case of 7-methylenebicyclo-2-heptene an unusual rearrangement was observed, with the formation of tricyclo4,6>-2-octene.
