Phosphonitrilic Compounds. V. Cyclized Products from the Reactions of Hexachlorocyclotriphosphazene (Phosphonitrilic Chloride Trimer) with Aromatic Dihydroxy, Dithiol, and Diamino Compounds

Harry R. Allcock, R. L. Kugel

Research output: Contribution to journalArticle

82 Citations (Scopus)

Abstract

Hexachlorocyclotriphosphazene, (NPCl2)3, reacted with 2,3-dihydroxynaphthalene, with 2,2ʹ-dihydroxybiphenyI, with toluene-3,4-dithiol, and with o-phenylenediamine, in the presence of base, to yield, respectively, tris(naphthyl-2,3-dioxy)-cyclotriphosphazene, tris(diphenyl-2,2ʹ-dioxj-)cyClotriphosphazene, tris(l-methylphenyl-3,4-dithio)cyclotriphosphazene, and tris(o-phenylenediamino)cyclotriphosphazene. When the reactant stoichiometry for the o-phenylenediamine reaction was changed, 1,1-o-phenylenediamino-3,3,5,5-tetrachlorocyclotriphosphazene was also obtained. The products were characterized by analytical, infrared, ultraviolet, and nmr methods, and the polymerization, inclusion, and polarographic behavior of specific compounds were examined. No evidence was found for interaction of the -π electrons of the cyclophosphazene system with the lone-pair or π electrons of the side groups.

Original languageEnglish (US)
Pages (from-to)1016-1020
Number of pages5
JournalInorganic Chemistry
Volume5
Issue number6
DOIs
StatePublished - Jan 1 1966

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trimers
thiols
Chlorides
chlorides
Electrons
products
Stoichiometry
toluene
stoichiometry
electrons
polymerization
Polymerization
inclusions
Infrared radiation
interactions
dithiol
hexachlorocyclotriphosphazene
1,2-diaminobenzene
diphenyl
2,3-dihydroxynaphthalene

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Inorganic Chemistry

Cite this

@article{12f6479ea9f342c28cac230b5c56e7f3,
title = "Phosphonitrilic Compounds. V. Cyclized Products from the Reactions of Hexachlorocyclotriphosphazene (Phosphonitrilic Chloride Trimer) with Aromatic Dihydroxy, Dithiol, and Diamino Compounds",
abstract = "Hexachlorocyclotriphosphazene, (NPCl2)3, reacted with 2,3-dihydroxynaphthalene, with 2,2ʹ-dihydroxybiphenyI, with toluene-3,4-dithiol, and with o-phenylenediamine, in the presence of base, to yield, respectively, tris(naphthyl-2,3-dioxy)-cyclotriphosphazene, tris(diphenyl-2,2ʹ-dioxj-)cyClotriphosphazene, tris(l-methylphenyl-3,4-dithio)cyclotriphosphazene, and tris(o-phenylenediamino)cyclotriphosphazene. When the reactant stoichiometry for the o-phenylenediamine reaction was changed, 1,1-o-phenylenediamino-3,3,5,5-tetrachlorocyclotriphosphazene was also obtained. The products were characterized by analytical, infrared, ultraviolet, and nmr methods, and the polymerization, inclusion, and polarographic behavior of specific compounds were examined. No evidence was found for interaction of the -π electrons of the cyclophosphazene system with the lone-pair or π electrons of the side groups.",
author = "Allcock, {Harry R.} and Kugel, {R. L.}",
year = "1966",
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doi = "10.1021/ic50040a015",
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T1 - Phosphonitrilic Compounds. V. Cyclized Products from the Reactions of Hexachlorocyclotriphosphazene (Phosphonitrilic Chloride Trimer) with Aromatic Dihydroxy, Dithiol, and Diamino Compounds

AU - Allcock, Harry R.

AU - Kugel, R. L.

PY - 1966/1/1

Y1 - 1966/1/1

N2 - Hexachlorocyclotriphosphazene, (NPCl2)3, reacted with 2,3-dihydroxynaphthalene, with 2,2ʹ-dihydroxybiphenyI, with toluene-3,4-dithiol, and with o-phenylenediamine, in the presence of base, to yield, respectively, tris(naphthyl-2,3-dioxy)-cyclotriphosphazene, tris(diphenyl-2,2ʹ-dioxj-)cyClotriphosphazene, tris(l-methylphenyl-3,4-dithio)cyclotriphosphazene, and tris(o-phenylenediamino)cyclotriphosphazene. When the reactant stoichiometry for the o-phenylenediamine reaction was changed, 1,1-o-phenylenediamino-3,3,5,5-tetrachlorocyclotriphosphazene was also obtained. The products were characterized by analytical, infrared, ultraviolet, and nmr methods, and the polymerization, inclusion, and polarographic behavior of specific compounds were examined. No evidence was found for interaction of the -π electrons of the cyclophosphazene system with the lone-pair or π electrons of the side groups.

AB - Hexachlorocyclotriphosphazene, (NPCl2)3, reacted with 2,3-dihydroxynaphthalene, with 2,2ʹ-dihydroxybiphenyI, with toluene-3,4-dithiol, and with o-phenylenediamine, in the presence of base, to yield, respectively, tris(naphthyl-2,3-dioxy)-cyclotriphosphazene, tris(diphenyl-2,2ʹ-dioxj-)cyClotriphosphazene, tris(l-methylphenyl-3,4-dithio)cyclotriphosphazene, and tris(o-phenylenediamino)cyclotriphosphazene. When the reactant stoichiometry for the o-phenylenediamine reaction was changed, 1,1-o-phenylenediamino-3,3,5,5-tetrachlorocyclotriphosphazene was also obtained. The products were characterized by analytical, infrared, ultraviolet, and nmr methods, and the polymerization, inclusion, and polarographic behavior of specific compounds were examined. No evidence was found for interaction of the -π electrons of the cyclophosphazene system with the lone-pair or π electrons of the side groups.

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