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Unusual Reactions of (+)‐Car‐2‐ene and (+)‐Car‐3‐ene with Aldehydes on K10 Clay
Authors:Irina V Il'ina  Konstantin P Volcho  Dina V Korchagina  Georgi E Salnikov  Alexander M Genaev  Elena V Karpova  Nariman F Salakhutdinov
Abstract: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.
Keywords:K10 Clay  Carenes  Aldehydes  Isobenzofuran  Catalysis  Density functional theory (DFT)
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