TY - JOUR
T1 - Synthesis of arylthiochlorocyclotriphosphazenes
AU - Kuroboshi, Manabu
AU - Mikasa, Masaki
AU - Tanaka, Hideo
N1 - Publisher Copyright:
© 2019 The Japan Institute of Heterocyclic Chemistry
PY - 2019
Y1 - 2019
N2 - – 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.
AB - – 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.
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U2 - 10.3987/COM-19-14100
DO - 10.3987/COM-19-14100
M3 - Article
AN - SCOPUS:85070763488
SN - 0385-5414
VL - 98
SP - 940
EP - 953
JO - Heterocycles
JF - Heterocycles
IS - 7
ER -