3,4-Bis- tert.-butylthio

Die Wahl des Losungsmittels bestimmt, welches Produkt bei der Cyclisierung von 1,2-Diamino-benzol mit Tris-[tert.-butylthio]-cyclopropenylium-perchlorat gebildet wird. In Methanol ent-steht 2-(1,2-Bis-[tert.-butylthio]-ethenyl)-benzimidazol (77%, tiber ein Allyl-Kation), im apro-tischen Dimethylformamid in einer inneren Michael-Addition 3,4-Bis-[tert.-butylthid -IH-l, 5-benzodiazepin (63% roh 100%)189. 

Chlorolysis. The action of chlorine on mercapto-l,2,4-thiadiazoles yields sulfenyl chlorides, sulfonyl chlorides, or chloro compounds, depending on the nature of the starting materials and the experimental conditions.147 Thus treatment of 3-tert-butylthio-l,2,4-thiadiazole with one mole of chlorine yields bis(l,2,4-thiadiazol-3-yl) disulfide (446) as a stable colorless solid. An excess of chlorine converts this to the 3-sulfonyl chloride (447), and further, with loss of sulfur dioxide, to the 3-chloro compound (448). Under appropriate conditions, the chlorolysis (to 448) may be performed in one operation (45%). The 3-sulfonyl chloride (447) yields sulfonamides nearly quantitatively the 3-chloro substituent in 448 is relatively inert (see Section IV.B).147... 

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