Reactions of lead tetra-acetate with substituted benzaldehyde 5-phenyl-1,2,4-triazol-3-ylhydrazones
- 1 January 1972
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 10,p. 1319-1323
- https://doi.org/10.1039/p29720001319
Abstract
In the reaction of lead tetra-acetate with substituted benzaldehyde 5-phenyl-1,2-4-triazol-3-ylhydrazones the presence of the triazole ring enhanced a cyclisation reaction leading to high yields of 3-aryl-6-phenyl-7H-s-triazolo-[4,3-b]-s-triazoles . Low yields of N-acetyl-N′-aroyl-N-(5-phenyl-1,2,4-triazol-3-yl) hydrazines were also isolated from a competitive acetoxylation reaction. The rates of the reaction were rapid, with second-order rate constants ca. 160–800 l mol–1 s–1 at 35° in glacial acetic acid. Substituents in the arylidene ring exerted a small influence (ρ=–0·60) on the reaction. The mechanism is discussed.Keywords
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