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 Научная публикация

Журнал

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

Вых. Данные

Год: 2010, Том: 93, Номер: 11, Страницы: 2135-2150 Страниц : DOI: 10.1002/hlca.201000145

Ключевые слова

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

Авторы

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

Организации

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

Опубликована в печати:	1 нояб. 2010 г.
Опубликована online:	11 нояб. 2010 г.

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