A novel Birch reduction of aromatic compounds using aqueous titanium trichloride: Anions of trans-10b,10c-dimethyl-2,7,10b,10c-tetrahydropyrene
Jiang, J. Lai, Y.-H.
Jiang, J.
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Abstract
The Birch reduction of 10b,10c-dimethyl-10b,10c-dihydropyrene 1 and anthracene could be predicted on the basis of their reduction potentials and achieved readily with aqueous titanium trichloride in near quantitative yields. Controlled reduction of a nitro group could be achieved under these conditions with the aromatic hydrocarbon remaining intact. The anion derived from the hexane obtained from reduction of 1 provided synthetic routes to derivatives of 1 inaccessible from direct substitution reactions of 1. Oxidative dimerization of the anion led to the formation of a series of interesting products. © 2003 Elsevier Science Ltd. All rights reserved.
Keywords
Anion, Birch reduction, Dihydropyrene, Oxidative coupling, Titanium trichloride
Source Title
Tetrahedron Letters
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Series/Report No.
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Date
2003-02-03
DOI
10.1016/S0040-4039(02)02785-5
Type
Article