On triazoles. XXXIII. The reaction of potassium triazolyldithiocarbonates with dihaloalkanes

The reaction of potassium (5-amino-3-Q-1,2,4-triazolyl)dithiocarbonates 2 with 1,ω-dihaloalkanes 7-10 to yield ω-haloalkyldithiocarbonates 11-12 , ω-alkylene-bis(dithiocarbonates) 13-15 and different by-products as the corresponding 7,8-dihydro1,2,4]triazolo1,5-c]1,3,5]thiadiazepine-5(9H)-thione ( 16 ), 7,8,9,10-tetrahy-dro1,2,4]triazolo1,5-c]1,3,5]thiadiazocine-5-thione ( 17 ) and 1,7-dihydro-5H-1,2,4-triazolo1,5-c]1,3,5]thiadi-azine-5-thione ( 22 ) derivatives all three representing novel ring systems were obtained. Repeating the reactions with dipotassium salts 3 the corresponding iminodithietans 18 , imino-1,3-dithiolanes 19 and imino-1,3-dithianes 20 were obtained. Unexpectively, the imino-1,3-dithiolanes ( 19 ) rearranged to the corresponding thiazolidines 24-27 under rather mild conditions. A possible mechanism is proposed for this rearrangement.