Nucleophilic substitution of hexachlorocyclotriphosphazene (HCCP)with arylthiol gave 2,2-bis(arylthio)-4,4,6,6-tetrachlorocyclotriphosphazene.Aminolysis of 2,2,4,4 -tet erachloro -6,6-bis(4-m ethoxyphenylt hio)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.

1997 substitution reactions substitution reactions O 0040 40 -052 Electrophilic Cyanations. Part 1. Synthesis of Thiocyanatoheteroarenes and Tosylheteroarenes from Mercaptoheteroarenes Using p-Toluenesulfonyl Cyanide. -A variety of mercapto-substituted heteroarenes (I) (15 examples) undergo electrophilic cyanation with tosyl cyanide (II) in THF to yield the thiocyanato derivatives (III). In DMF the tosylheteroarenes ( IV) are obtained. Using BrCN for electrophilic cyanation gives symmetrical disulfides as side products. Furthermore, electrophilic cyanation of the quinazolinone (VI) gives the N-substituted product ( VII) and 2-mercaptoaniline (VIII) yields the benzothiazole (IX) via cyclization of the primary 2-thiocyanatoaniline. -(MIYASHITA, A.; NAGASAKI, I.; KAWANO, A.; SUZUKI, Y.; IWAMOTO, K.; HIGASHINO, T.; Heterocycles 45 (1997) 4, 745-755; Sch. Pharm. Sci., Univ. Shizuoka, Yada, Shizuoka 422, Japan; EN)