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New aromatic rearrangement accompanying ring closure of 2-arylpropylidenemalonodinitriles to 1-aminonaphthalene-2-carbonitriles

✍ Scribed by Janusz J Sepiol; Jaroslaw Wilamowski

Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 57 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)00938-8

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✦ Synopsis

Cyclization and a rearrangement in concentrated sulfuric acid of 2-(4-substituted-phenyl)propylidenemalonodinitriles (1) into 1-amino-4-methyl-6-substituted-naphthalene-2-carbonitriles (5) appears to involve a series of steps such as ipso electrophilic attack of the protonated nitrile function on the para position of the phenyl group, opening of a spirobenzenium cation or its transformation, and ring reclosure to the naphthalene framework with participation of the secondary alkyl carbocation as an active electrophile.

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