Über Chalkogenolate. 166. Umsetzungen von Hydrazin mit Kohlenstoffdisulfid 5. Versuche zur Darstellung von Estern der 1,2-Hydrazin-bis(dithiocarbonsäuren) [1]

On Chalcogenolates. 166. Reactions of Hydrazine with Carbon Disulfide. 5. Attempts to Prepare Esters of 1,2-Hydrazine-bis(dithiocarboxylic Acids) Possible reactions to synthesize esters of 1,2-hydrazine-bis(dithiocarboxylic acids) are described:

• 1 The reaction of K₂[S₂C? NH? NH? CS₂] with H₃CI preponderantly forms 2,5-dimethylthio-1,3,4-thiadiazole Ia and a small quantity of bis(methylthio)-ketazine II (formula see ?Inhaltsübersicht”?).
• 2 Hydrazine reacts with Cl? CS? SC₂H₅ to give exclusively compound Ib
• 3 The reaction between K₂[S₂C=N? NH? CS? SCH₃] and H₃CI yields 94% compound Ia and 6% compound II
• 4 K₂[S₂C=N? NH? CS? SCH₃] reacts with C₆H₅? CH₂Br to form a mixture containing 25% dibenzyl sulfide, 15% 2,5-dibenzylthio-1,3,4-thiadiazole I e, and 60% 2-methylthio-5-benzylthio-1,3,4-thiadiazole I d

The compounds Ia , Id and II have been characterized by means of diverse spectroscopic methods. The mechanism of the formation of compounds I has been discussed.