Formation and X-ray Structures of Eight- and Sixteen-Membered Rings (ArC)nN2n(SPh)n [n = 2, Ar = 4-XC6H4 (X = Br, CF3); n = 4, Ar = 4-BrC6H4] and the Electronic Structures of (HC)2N4(SH)2 and (HC)2N4(SH)22-

Optimum yields of heterocyclic products are obtained when the reaction of 4-XC6H4CN2(SiMe3)3 (X = Br, CF3) with PhSCl in a 1:3 molar ratio in CH2Cl2 is carried out at -100°C followed by the mixture being warmed to -70°C for 16 h. Under these conditions the eight-membered rings (4-XC6H4)2C2N4S 2Ph2 (1b, X = Br; 1c, X = CF3) are obtained in 64 and 80% yields, respectively, in addition to the purple diazenes Z,E,Z-PhSN(4-XC6H4)-CN=NC(C6H 4X-4)NSPh …