92760-17-3Relevant articles and documents
MOLECULAR REARRANGEMENTS OF CARYOPHYLLENE AND ISOCARYOPHYLLENE 4,5-EPOXIDES IN SUPERACIDIC MEDIA
Nisnevich, G. A.,Korchagina, D. V.,Makal'skii, V. I.,Dubovenko, Zh. V.,Barkhash, V. A.
, p. 441 - 453 (2007/10/02)
Enantiomeric stable carbocations were generated from the epimeric pair of optically active isocaryophyllene 4β,5β- and 4α,5α-epoxides in the superacid.The subsequent molecular rearrangement path is determined by participation of the ? and ? bonds in opening of the epoxide ring.For the case of caryophyllene 4β,5α- and 4α,5β-epoxides it was shown that rearrangement to compounds with the clovane or caryolane skeleton respectively is possible.The rearrangement of a compound of the caryophyllane type to compounds of the selinane group was realized for the first time.For the case of caryophyllene 4β,5α-epoxide it was shown that the generation temperature of the ions has a significant effect on the preferred position of the cationic center.