Reaction of Phenacyltriphenylarsonium Bromides with N-Methylaniline and N,N-Dimethylaniline

Article abstract of DOI:10.1246/bcsj.53.2423

Reaction of phenacyltriphenylarsonium bromide with N-methylaniline furnished 2-phenylindole predominantly together with 1-methyl-2-phenylindole.The corresponding reaction of the arsonium salt with N,N-dimethylaniline did not give any indole, instead a simple nucleophilic substituted product, α-4'-(dimethylamino)deoxybenzoin was obtained.But, the latter reaction on being carried out in presence of hydrobromic acid afforded 1-methyl-2-phenylindole by the demethylation of N,N-dimethylaniline.