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‐dihydro[1,2,4]triazolo[1,5‐ c ][1,3,5]thiadiazepine‐5(9 H )‐thione ( 16 ), 7,8,9,10‐tetrahy‐dro[1,2,4]triazolo[1,5‐ c ][1,3,5]thiadiazocine‐5‐thione ( 17 ) and 1,7‐dihydro‐5 H ‐1,2,4‐triazolo[1,5‐ 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.