Journal
HELVETICA CHIMICA ACTA
Volume 90, Issue 2, Pages 353-368Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/hlca.200790042
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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.
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