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Original Articles

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

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Pages 287-294 | Received 13 Feb 1996, Published online: 04 Oct 2006
 

Abstract

The reaction of N-p-ethoxyphenylanthranilic acid 1 with phosphorus trichloride furnished the 2-chloro-1,3,2-benzoxazaphosphorin-6-one 2, which was allowed to react with bis-(2-chloroethyl)amine hydrochloride to form 3 by substitution at phosphorus. Treatment of 3 and the previously known N-p-fluorobenzyl-, N-p-chlorobenzyl- and N-o-chlorobenzyl-substiuted 1,3,2-benzodiazaphosphorin-4-ones 4–6 with the hydrogen peroxide/urea 1:1 adduct led to the phosphoryl species 7–10. The phosphoryl derivatives 14–16 were obtained by hydrolysis of the previously known λ3P-chloro derivatives 11–13 with small amounts of water. For the N-p-fluorobenzyl substituted compound 14 a single crystal X-ray structure determination showed a weak intermolecular P—H … O contact.

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