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Aminium salt induced cyclodimerization of stilbenes in 1,1,1,3,3,3-hexafluoropropan-2-ol

✍ Scribed by Francesco Ciminale; Luigi Lopez; Gianluca M Farinola

Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 238 KB
Volume: 40
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(99)01447-1

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✦ Synopsis

The aminium salt induced reactions of stilbenes (la-d), affording a mixture of indane (2a--e) and/or tetrahydronaphthalene derivatives (3a,c,d), were found to occur with remarkably higher efficiency in 1,1,1,3,3,3hexafluoropropan-2-ol (HFP) than, if at all, in dichloromethane (DCM) solutions. This solvent effect seems consistent with an electron-transfer mechanism via radical cations 1 ÷" that chemical evidence indicates to be favoured over an alternative electrophilic mechanism involving carbocations IH +.

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