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

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

Journal

Helvetica Chimica Acta
ISSN: 0018-019X , E-ISSN: 1522-2675

Output data

Year: 2010, Volume: 93, Number: 11, Pages: 2135-2150 Pages count : DOI: 10.1002/hlca.201000145

Tags

Aldehydes; Carenes; Catalysis; Density functional theory (DFT); Isobenzofuran; K10 Clay

Authors

Il'ina Irina V. ¹ , Volcho Konstantin P. ¹ , Korchagina Dina V. ¹ , Salnikov Georgi E. ¹ , Genaev Alexander M. ¹ , Karpova Elena V. ^1,2 , Salakhutdinov Nariman F. ¹

Affiliations

1	(Данные Web of science) Russian Acad Sci, N N Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Novosibirsk 630090, Russia

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

Il'ina I.V. , Volcho K.P. , Korchagina D.V. , Salnikov G.E. , Genaev A.M. , Karpova E.V. , Salakhutdinov N.F.
Unusual Reactions of (+)-Car-2-ene and (+)-Car-3-ene with Aldehydes on K10 Clay
Helvetica Chimica Acta. 2010. V.93. N11. P.2135-2150. DOI: 10.1002/hlca.201000145 WOS Scopus РИНЦ

Published print:	Nov 1, 2010
Published online:	Nov 11, 2010

Web of science	WOS:000285069500003
Scopus	2-s2.0-78549266518
Elibrary	16631420
OpenAlex	W2002701112