The reactions of diorganophosphides with organic halides have been examined by 31P CIDNP and product analysis. These reactions are shown to proceed in part by a radical mechanism and in part by a competing nonradical path. The preference for one mechanism or the other is highly dependent on the nature of the organic group, halide, and substituents bound to phosphorus. Thus, alkyl, allyl, and benzyl iodides and bromides react, to some ...
