Remarkable selectivity in the reaction of l‐trityl‐2‐lithioimidazoles with t ‐butyl halogenoacetates

2‐Lithio‐1‐triphenylmethylimidazoles react with t ‐butyl halogenoacetates to give a variety of products, the nature of which is cleanly determined by the halogen atom. With chloroacetate the products are chloromethyl ketones, while bromacetate gives di‐ t ‐butyl imidazolesuccinates, and iodoacetate yields iodoimidazoles. In each case 50% of the parent triphenylmethylimidazole is recovered from the reaction. When the triphenylmethyl substituent is replaced by the N,N ‐dimethylsulfamoyl group, reaction with bro‐moacetate is suppressed, but t ‐butyl chloroacetate and iodoacetate again give chloroketones and aryl iodides respectively.