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Reactions of Allyl Alcohols of the Pinane Series and of Their Epoxides in the Presence of Montmorillonite Clay
Author(s) -
Il'ina Irina V.,
Volcho Konstantin P.,
Korchagina Dina V.,
Barkhash Vladimir A.,
Salakhutdinov Nariman F.
Publication year - 2007
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200790042
Subject(s) - chemistry , reactivity (psychology) , montmorillonite , epoxide , aldehyde , bentonite , organic chemistry , isomerization , alcohol , catalysis , medicine , paleontology , alternative medicine , pathology , biology
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.