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|Title:||A novel Birch reduction of aromatic compounds using aqueous titanium trichloride: Anions of trans-10b,10c-dimethyl-2,7,10b,10c-tetrahydropyrene||Authors:||Jiang, J.
|Issue Date:||3-Feb-2003||Citation:||Jiang, J., Lai, Y.-H. (2003-02-03). A novel Birch reduction of aromatic compounds using aqueous titanium trichloride: Anions of trans-10b,10c-dimethyl-2,7,10b,10c-tetrahydropyrene. Tetrahedron Letters 44 (6) : 1271-1274. ScholarBank@NUS Repository. https://doi.org/10.1016/S0040-4039(02)02785-5||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.||Source Title:||Tetrahedron Letters||URI:||http://scholarbank.nus.edu.sg/handle/10635/75455||ISSN:||00404039||DOI:||10.1016/S0040-4039(02)02785-5|
|Appears in Collections:||Staff Publications|
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