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Acid Catalysis in the Aminium Hexachloroantimonate‐Induced Cyclodimerization of 1‐Aryl‐1‐phenylethylenes
Author(s) -
Ciminale Francesco,
Lopez Luigi,
Farinola Gianluca M.,
Sportelli Stefano,
Nacci Angelo
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200211)2002:22<3850::aid-ejoc3850>3.0.co;2-y
Subject(s) - chemistry , aryl , catalysis , organic chemistry , medicinal chemistry , photochemistry , combinatorial chemistry , alkyl
The aminium hexachloroantimonate‐induced cyclodimerization of various 1‐aryl‐1‐phenylethylenes, affording regioisomeric indane derivatives via a carbocation mechanism, was found to occur in a similar manner when SbCl 5 was used instead of the aminium salt, hence antimony pentachloride is proposed as the acid catalyst. Its formation in the reactions with aminium hexachloroantimonates occurs by the oxidation of the SbCl 6 − anion by its aminium counterion. Moreover, this cyclodimerization reaction occurs with much higher efficiency and enhanced regioselectivity in 1,1,1,3,3,3‐hexafluoropropan‐2‐ol (HFP) than in dichloromethane. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)