Abstract: The reactivity of allyl alcohols of the pinane series and of their epoxides in the presence of montmorillonite clay in intra- and intermolecular reactions was studied. Mutual transformations of (+)-trans-pino-carveol ((+)-2) and (-)-myrtenol ((-)-3a) were major reactions of these compounds on askanite-bentonite clay (Schemes 1 and 2). However, the two reactions gave different isomerization products, indicating that the reactivity of the starting alcohol (+)-2 or (-)-3a was different from that of the same compound (+)-2 or (-)-3 formed in the course of the reactions. (-)-cis- and (+)-trans-Verbenol ((-)-16 and (+)-12, resp.), as well as (-)-cis-verbenol epoxide ((-)-20) reacted with both aliphatic and aromatic aldehydes on askanite-bentonite clay giving various heterocyclic compounds (Schemes 4, 5 and 7); the reaction path depended on the structure of both the terpenoid and the aldehyde.

Cite: Il'ina I.V. , Volcho K.P. , Korchagina D.V. , Barkhash V.A. , Salakhutdinov N.F.
Reactions of allyl alcohols of the pinane series and of their epoxides in the presence of montmorillonite clay
Helvetica Chimica Acta. 2007. V.90. N2. P.353-368. DOI: 10.1002/hlca.200790042 WOS Scopus РИНЦ

Dates:

Published print:

Feb 1, 2007

Identifiers:

Web of science	WOS:000244963700015
Scopus	2-s2.0-34250679787
Elibrary	13547093
OpenAlex	W1971498415

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