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-pinocarveol ((+)-2) and (À)-myrtenol ((À)-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 (À)-3a was different from that of the same compound (+)-2 or (À)-3 formed in the course of the reactions. (À)-cis-and (+)-trans-Verbenol ((À)-16 and (+)-12, resp.), as well as (À)-cis-verbenol epoxide ((À)-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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