367912-35-4Relevant academic research and scientific papers
New aromatic rearrangement accompanying ring closure of 2-arylpropylidenemalonodinitriles to 1-aminonaphthalene-2-carbonitriles
Sepiol, Janusz J,Wilamowski, Jaroslaw
, p. 5287 - 5289 (2007/10/03)
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.
