Synthesis of arylthiochlorocyclotriphosphazenes

Manabu Kuroboshi, Masaki Mikasa, Hideo Tanaka

Research output: Contribution to journalArticle

Abstract

– We investigated the reaction between hexachlorocyclotriphosphazene ((NPCl2)3: HCCP) and thiols in the presence of bases. In MeCN/Et3N, two and/or four arylthio units were introduced in gem-mode selectively by controlling the amount of thiols: thus, HCCP was treated with 2 and/or 4 equivalents of ArSH/Et3N in MeCN to afford 2,2-dithiolated and/or 2,2,4,4-tetrathiolated products, respectively. Neither mono-thiosubstituted products, tri-thiosubstituted products, nor regioisomers (non-geminal products) were obtained. In contrast, when other solvents such as THF and Et2O or other bases such as NaH or K2CO3 were used, a mixture of dithiolated products, tetrathiolated products, and hexathiolated products was obtained.

Original languageEnglish
Pages (from-to)940-953
Number of pages14
JournalHeterocycles
Volume98
Issue number7
DOIs
Publication statusPublished - Jan 1 2019

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Sulfhydryl Compounds
Gems
potassium carbonate
hexachlorocyclotriphosphazene

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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Synthesis of arylthiochlorocyclotriphosphazenes. / Kuroboshi, Manabu; Mikasa, Masaki; Tanaka, Hideo.

In: Heterocycles, Vol. 98, No. 7, 01.01.2019, p. 940-953.

Research output: Contribution to journalArticle

Kuroboshi, Manabu ; Mikasa, Masaki ; Tanaka, Hideo. / Synthesis of arylthiochlorocyclotriphosphazenes. In: Heterocycles. 2019 ; Vol. 98, No. 7. pp. 940-953.
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