SRN1 SYNTHESES OF BIS(PHENYLTHIO)- AND DICYANO-NAPHTHALENES VIA DIAZOSULFIDES

Article abstract of DOI:10.1016/S0040-4020(01)89785-4

The reactions of bromonaphthalenediazonium tetrafluoroborates (6a,b and 11a,b) with sodium benzenethiolate in DMSO give, through the preliminary formation of the corresponding diazosulfides (7a,b and 12a,b) bis(phenylthio)naphthalenes (8a,b and 13a,b) deriving from substitution of both the diazo group and the bromine.Isolated diazosulfides (7a,b and 12a,b) likewise furnish satisfactory yields of dinitriles (9a,b and 14a,b) by reaction with excess tetrabutylammonium cyanide in DMSO under photostimulation by a sunlamp.The intervention of an S_RN1 process accounting for the formation of the disubstitution products is postulated.