NUCLEOPHILIC SUBSTITUTION of 2,2-BIS(ARYLTHIO)-4,4,6,6-TETRACHLOROCYCLOTRIPHOSPHAZENE with AMMONIA, PHENOXIDE, and THIOPHENOXIDE

Manabu Kuroboshi, Ayako Ueno, Ayane Kawano, Hideo Tanaka

Research output: Contribution to journalArticlepeer-review

Abstract

Nucleophilic substitution of hexachlorocyclotriphosphazene (HCCP) with arylthiol gave 2,2-bis(arylthio)-4,4,6,6-tetrachlorocyclotriphosphazene. Aminolysis of 2,2,4,4-teterachloro-6,6-bis(4-methoxyphenylthio)- cyclotriphosphazene with gaseous ammonia gave gem-disubstituted 2,2-diamino-4,4-dichloro-6,6-bis(4-methoxyphenylthio)cyclotriphosphazene in Et2O and tetrasubstituted 2,2,4,4-tetraamino-6,6-bis(4-methoxyphenylthio)- cyclotriphosphazene in acetonitrile, respectively. The reaction of 2,2,4,4-teterachloro-6,6-bis(4-methoxyphenylthio)cyclotriphosphazene with 4-chlorophenol gave a mixture of gem-disubstituted 2,2-dichloro-4,4-bis(4-chlorophenoxy)-6,6-bis(4-methoxyphenylthio)cyclotripho-sphazene and tetrasubstituted 2,2,4,4-tetrakis(4-chlorophenoxy)-6,6-bis(4- methoxyphenylthio)cyclotriphosphazene, whose ratio depended on the reaction solvent. On the other hand, in reaction of 2,2-bis(arylthio)-4,4,6,6-tetrach- lorocyclotriphosphazene with another arylthiol, ArS-groups were scrambled.

Original languageEnglish
Pages (from-to)69-84
Number of pages16
JournalHeterocycles
Volume104
Issue number1
DOIs
Publication statusPublished - 2021

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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