PREPARATION OF N-PHOSPHORYLATED NITROGEN MUSTARDS WITH THE BENZODIAZAPHOSPHORINONE AND OXAZAPHOSPHORINONE RING-SYSTEMS - HYDROLYSIS OF 2-CHLORO BENZODIAZAPHOSPHORINONES

The reaction of N-p-ethoxyphenylanthranilic acid 1 with phosphorus tri chloride furnished the 2-chloro-1,3,2-benzoxazaphosphorin-6-one 2, whi ch was allowed to react with bis-(2-chloroethyl)amine hydrochloride to form 3 by substitution at phosphorus. Treatment of 3 and the previous ly known N-p-fluorobenzyl-, N-p-chlorobenzyl- and N-o-chlorobenzyl-sub stituted 1,3,2-benzodiazaphosphorin-4-ones 4-6 with the hydrogen perox ide/urea 1:1 adduct led to the phosphoryl species 7-10. The phosphoryl derivatives 14-16 were obtained by hydrolysis of the previously known lambda(3)P-chloro derivatives 11-13 with small amounts of water For t he N-p-fluorobenzyl substituted compound 14 a single crystal X-ray str ucture determination showed a weak intermolecular P-H ... O contact.