Abstract
The reacton of nitriles with hydrazine hydrate in the presence of sulfer compounds offers a convenient synthetic method of 3, 6-disubstituted-1, 2-dihydro-s-tetrazines. Sulfur, mercaptans, disulfides and polysulfides are effective catalysts for the reaction at temperatures in the range of about 20° to 80°C. Mercaptoacetic acid and mercaptoethanol were the most effective catalysts among them. Their catalytic ro1e is discussed in terms of neighboring group participation.The additions of large amounts of amines in the reaction mixture of benzonitrle, hydrazine hydrate and mercaptoacetic acid did not affect the yield of the product, but, when sodium hydroxide was added, none of the products was formed.On the basis of these observatlons, a mechanism of the reaction and also the catalytic role of some sulfur compounds were discussed.
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