Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Titanium(III) Chloride Mediated Reduction of 1-Nitro-2-phenylethenes
Akira SeraShoji FukumotoMasako TamuraKiyoshi TakabatakeHiroaki YamadaKuniaki Itoh
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1991 Volume 64 Issue 6 Pages 1787-1791

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Abstract

The reaction of 1-nitro-2-phenylethenes (β-nitrostyrenes) with aqueous titanium(III) chloride afforded substituted pyrroles in addition to the expected reduction products, oximes and carbonyl compounds. 2-Substituted 1-nitro-2-phenylethenes yielded divinylamine derivatives instead of pyrroles. The reaction mechanism has been rationalized by taking account of the electron transfer from titanium(III) species to the nitro olefins, followed by protonation, dimerization, cyclization, and/or hydrolysis.

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