Polarisation by cation formation (e.g., by protonation or by oxocarbonium ion formation) exerts a distinct and systematic effect on the selectivity of radical chlorination of aliphatic acids, amines, and alcohols. A qualitative correlation is demonstrated between the magnitude of deshielding of a given proton (as expressed by the downfield shift in the l H n.m.r. spectrum) and its '* deactivation '* as indicated by diminished rate of its abstraction by chlorine atoms. A convenient method is described for the preparation of new and known aliphatic mono-and polychloro-amines. New Jersey, U.S.A. * This reactor was designed and built with the valuable cooperation of Mr. R. Geiger of our machine shop.
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