PREPARATION OF N-PHOSPHORYLATED NITROGEN MUSTARDS WITH THE BENZODIAZAPHOSPHORINONE AND OXAZAPHOSPHORINONE RING-SYSTEMS - HYDROLYSIS OF 2-CHLORO BENZODIAZAPHOSPHORINONES
I. Neda et al., PREPARATION OF N-PHOSPHORYLATED NITROGEN MUSTARDS WITH THE BENZODIAZAPHOSPHORINONE AND OXAZAPHOSPHORINONE RING-SYSTEMS - HYDROLYSIS OF 2-CHLORO BENZODIAZAPHOSPHORINONES, Phosphorus, sulfur and silicon and the related elements, 113(1-4), 1996, pp. 287-294
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.