Accession Number:

ADA158449

Title:

Syntheses of Novel Nitrogen and Phosphorus Heterocycles.

Descriptive Note:

Final rept. 1 Mar 82-28 Feb 85,

Corporate Author:

ULTRASYSTEMS INC IRVINE CA

Report Date:

1985-04-26

Pagination or Media Count:

62.0

Abstract:

1-Dichlorophospha-3,5-perfluoro-n-heptyl or perfluoroalkylether-2,4,6-tri azines were synthesized by interaction of imidoylamidines with phosphorus pentachloride. In a parallel approach, 1,3-bisphenylchlorophospha-5-perfluoroalkyl or perfluoroalkylether-2,4,6-triazines were obtained from the reaction of amidines with imido-diphenyl-diphosphinic acid pentachloride. Replacement of chlorine by thiophenyl and azido groups proceeded readily. Di-phenylchlorophospha-s-triazine was found to undergo further reaction with amidine in a 12 ratio. The existence of stereo-isomerism was indicated. The thiophenyl-substituted phospha-s-triazines functioned as corrosion and oxidation inhibitors in perfluoroalkylether fluids however, their thermal and thermal oxidative stability was lower than that of the phenyl analogues. Both the mono- and diphospha-s-triazines were completely degraded in 24 hr at 316 C in nitrogen diphenylsulfide was one of the major products. Mass spectral analysis of the phenyl-free phospha-s-triazines revealed that the specific breakdown patterns are ring specific not phenyl-substituent dependent. Perfluoro-n-octanonitrile was found to react with aniline both in the absence and presence of solvents. Treatment of perfluoro-n-octanonitrile with phenylphosphine gave tetraphenyltetraphosphine and a spectrum of reduction and interaction products of perfluorooctanonitriles, as well as phenylphosphine addition compounds.

Subject Categories:

  • Organic Chemistry

Distribution Statement:

APPROVED FOR PUBLIC RELEASE