
%0 Journal Article
%A Barnes, CS 
%A Halbert, EJ 
%A Goldsack, RJ 
%T The dimerization of anils of pyridine aldehydes catalysed by cyanide ion
%J Australian Journal of Chemistry
%D 1973/09/01
%V 26
%N 9
%P 2027-2034
%K 
%R https://doi.org/10.1071/CH9732027
%U https://www.publish.csiro.au/paper/CH9732027 
%X The three isomeric N-(pyridylmethylene)anilines (1; Ar? = pyridyl, Ar = phenyl) dimerized in Me2SO with NaCN to give the enediamines (2). Only when Ar? = 3-pyridyl did this spontaneously dehydrogenate to the bis(phenylimino) compound which was hydrolysed to 3,3?-pyridil. The 4- pyridyl enediamine (2; Ar? = 4-pyridyl, Ar = phenyl) formed a 1 : 1 adduct with Me2SO. It was oxidized in poor yield to the stable bis(phenylimino) compound. The 2-pyridyl enediamine (2; Ar? = 2- pyridyl, Ar = phenyl) was oxidized with chloranil. Under standard conditions attempted dimerization of (1; Ar? = 4-pyridyl, Ar = 4- methoxyphenyl) gave a [(4?-methoxyphenyl)imino](4-pyridyl)acetonitrile (7).     A series of monophenylimino derivatives of 2,2?-pyridil, and some anilides of isonicotinic acid, were prepared. 
