Abstract
On photolysis in methanol the diarylphosphinic azides AR 2P(O)N 3 (Ar = phenyl, p-tolyl, p-anisyl, p-chlorophenyl) rearragement with loss of nitrogen to form (monemeric) metaphosphonimidates which are trapped by the solvent to give methyl NP-diarylphosphonamidates (7) (41–53%). Diarylphosphinic amides (18–42%) are also usually formed, presumably from (triplet) nitrenes. The limited evidence available suggests that the rearrangements take place directly from the photo-excited azides rather than via (singlet) nitrene intermediates. One of the products of rearrangement, methyl NP-di( p-chlorophenyl)phosphonamidate, suffers extensive photochemical dechlorination giving methyl N-phenyl-P- p-chlorophenylphosphonamidate.
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