Reactions of Allyl Alcohols of the Pinane Series and of Their Epoxides in the Presence of Montmorillonite Clay |
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Authors: | Irina?V Il'ina Konstantin?P Volcho Dina?V Korchagina Vladimir?A Barkhash Nariman?F Salakhutdinov |
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Institution: | N.?N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, 630090 Novosibirsk, Russian Federation, (fax: +?7?383?3309752) |
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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‐pinocarveol ((+)‐ 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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Keywords: | Clay Pinene alcohols Epoxides Aldehydes Montmorillonite |
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