1,3,5-Triazines. Part VIII. The reactions of cyanuric chloride with NN-dialkylnaphthylamines and O-alkyl naphthyl ethers

Abstract

The reactions of cyanuric chloride with NN-dimethyl-, NN-diethyl-and NN-diethyl-2-methyl-1-naphthylamines have been investigated. Two types of products were obtained, N-alkyl-N-(1-naphthyl) aminodichloro-1,3,5-triazines and 4′-(NN-dialkylamino-1-naphthyl)dichloro-1,3,5-triazines. NN-Diethyl-2-naphthylamine under comparable conditions gave three products, N-ethyl-N-(2-naphthyl)aminodichloro-1,3,5-triazine, bis-(N-ethyl-N-2′-naphthylamino)chloro-1,3,5-triazine, and (2-NN-diethylamino-1-naphthyl)dichloro-1,3,5-triazine. This reaction has given the first, and so far only, example of the triazine electrophile entering an aromatic ring at any position other than para to the dialkylamino-group. This type of reaction which up to now has been confined to tertiary arylamines is now extended to O-alkyl naphthyl ethers. The latter require much higher temperatures for reaction, and give exclusively nuclear substituted products. The factors influencing the relative proportions of the compounds obtained are discussed. The determination of the structures by means of i.r., u.v., and 1H n.m.r. spectroscopy is described.