99881-55-7Relevant articles and documents
STEREOHCEMICALLY ABNORMAL CYCLIZATION OF CARYOPHYLLENE BY THE ACTION OF MERCURY(II) ACETATE
Tkachev, A. V.,Gatilov, Yu. V.,Bagryanskaya, I. Yu.,Shakirov, M. M.,Mamatyuk, V. I.,et al.
, p. 490 - 503 (2007/10/02)
The products from mercuration-demercuration of the sesquiterpene hydrocarbon caryophyllene by the action of mercury(II) acetate in acetic acid were studied.The chemical structure of the main reaction product 1,4,4-trimethyltricyclo2.5>dodec-8-ene was determined by 13C NMR on the basis of an analysis of the spin-spin coupling constants 1J (13C-13C).The stereochemical structure was established by x-ray crystallographic analysis of the corresponding epoxide.A mechanism is proposed for the isomerization of caryophyllene into compounds with the tricyclo2,5>dodecane skeleton, including intramolecular attack by the mercury-containing function at the C=C bond.It was established that biomimetic cyclization of caryophyllene to β-panasinsene occurs with mercury(II) acetate in acetic acid (followed by reductive demercuration).