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Unusual Reactions of (+)-Car-2-ene and (+)-Car-3-ene with Aldehydes on K10 Clay

โœ Scribed by Irina V. Il'ina; Konstantin P. Volcho; Dina V. Korchagina; Georgi E. Salnikov; Alexander M. Genaev; Elena V. Karpova; Nariman F. Salakhutdinov


Publisher
John Wiley and Sons
Year
2010
Tongue
German
Weight
247 KB
Volume
93
Category
Article
ISSN
0018-019X

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โœฆ Synopsis


Abstract

The reactions of (+)โ€carโ€2โ€ene (1) and (+)โ€carโ€3โ€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 cisโ€configured at the ringโ€fusion site; the fact was established by means of quantumโ€chemical calculations and NMR data. It appeared that the behavior of the 2โ€‰:โ€‰3 mixture 1/2 in reactions with aldehydes in the presence of K10 clay differed substantially from the reactivities of the corresponding individual monoterpenes.


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