A variety of benzylidene sugars containing vicinal trichloroacetimidoyl groups have been oxidized by N-bromosuccinimide, to ascertain which structural features are necessary for neighbouring group participation from the iminoester in the opening of the transitory benzoxonium ion. The results indicate that the trichloroacetimidoyl group closely resembles the acyl group in its ability to participate, and that the resulting iminoester is strongly ...
