Sulphur nitrides in organic chemistry. Part 8. Reaction of tetrasulphur tetranitride with Grignard reagents and organolithium compounds

Abstract

The reaction of tetrasulphur tetranitride (N4S4)(1) with Grignard reagents (2a–h) and organolithium compounds (10a–h) was investigated. It was found that the reaction of (1) with (2) gave the corresponding disulphides (4a–h) in good yields together with 1,5-diaryl-1,3,5,2,4-trithiadiazapenta-2,3-dienes (3a–c), bisarylamino sulphides (5a and b), ammonium thiosulphates (6a–e), and thiosulphonates (7a–d). Reaction of (1) with (10a–f), generated from benzyl sulphides, afforded diaryl disulphides (4a, b, and e) in moderate yields accompanied by trans-stilbenes (11a and b) and 1,2-bisphenylthio-1,2-diarylethanes (12a and b). Reaction of (1) with diphenyl(phenylthio)methyl-lithium (10g), gave diphenyl disulphide (4a), the tetraphenylethylene (11c), and benzophenone (13a), while reaction of sulphur with (10g) afforded 1,2-epithio-1,1,2,2-tetraphenylethane (15) in 52% yield besides (4a), (11c), and (13c). Reaction of (1) with 9-phenylthiofluoren-9-yl-lithium (10h) gave (4a), bifluorenylidene (11d), 1,1′-bisphenylthiobifluorenyl (12c), fluorenone (13b), and fluorenylideneaminosulphenamide (14).