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Unusual Reactions of (+)‐Car‐2‐ene and (+)‐Car‐3‐ene with Aldehydes on K10 Clay
Author(s) -
Il'ina Irina V.,
Volcho Konstantin P.,
Korchagina Dina V.,
Salnikov Georgi E.,
Genaev Alexander M.,
Karpova Elena V.,
Salakhutdinov Nariman F.
Publication year - 2010
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.201000145
Subject(s) - chemistry , ene reaction , cyclopropane , aldehyde , ring (chemistry) , montmorillonite , protonation , organic chemistry , medicinal chemistry , catalysis , ion
The reactions of (+)‐car‐2‐ene ( 1 ) and (+)‐car‐3‐ene ( 2 ) with aldehydes in the presence of montmorillonite clay were studied for the first time ( Schemes 3 and 5 ). The major products of these reactions are optically active, substituted hexahydroisobenzofurans, probably formed as a result of an attack of the protonated aldehyde at the cyclopropane ring. Quite unexpectedly, the products are cis ‐configured at the ring‐fusion site; the fact was established by means of quantum‐chemical calculations and NMR data. It appeared that the behavior of the 2 : 3 mixture 1 / 2 in reactions with aldehydes in the presence of K10 clay differed substantially from the reactivities of the corresponding individual monoterpenes.