Adamantylazoles: VIII. Acid-catalyzed adamantylation of 1,2,4-triazol-5-ones

3-R-1,2,4-Triazol-5-ones are adamantylated in sulfuric acid. The reaction involves the N¹ atom of the ring. 4-Adamantyl-1-methyl-, 1-adamantyl-4-methyl-, and 1,4-diadamantyl-1,2,4-triazol-5-ones were also prepared. Therewith, it was found that N¹ exhibits a higher reactivity than N⁴.Translated from Zhurnal Obshchei Khimii, Vol. 74, No. 8, 2004, pp. 1377–1382.Original Russian Text Copyright © 2004 by Amandurdyeva, Saraev, Kuzmina, Golod.For communication VII, see [1].This revised version was published online in April 2005 with a corrected cover date.     

Adamantylazoles: X. Reactions of 1,2,4-Triazole-3-thione with 1-Adamantanol in Acid Solutions

1,2,4-Triazole-3-thione reacts with 1-adamantanol in concentrated sulfuric acid to form 1-(1-adamantyl)-1,2,4-triazole-3-thione, which transforms into 1-(1-adamantyl)-3-(1-adamantyl)sulfanyl-1,2,4-triazole or is oxidized with atmospheric oxygen dissolved in sulfuric acid into 3,3′-disulfanediylbis[1-(1-adamantyl)- 1,2,4-triazole]. 3-(1-Adamantyl)sulfanyl-1,2,4-triazole was prepared by adamantylation of 1,2,4-triazole-3-thione in a mixture of phosphoric and acetic acid (weight ratio 4 : 1).