Oxidative cyclisation of ketone thiosemicarbazones. Part II. Derivatives of phenoxyacetone

Abstract

Oxidative cyclisation of phenoxyacetone (4-phenyl)thiosemicarbazone to 5-methyl-5-phenoxymethyl-4-phenyl-Δ¹-1,2,4-triazoline-3-thione was accompained by a rearrangement giving 3-mercapto-5-methyl-1-phenoxy-methyl-4-phenyl-1,2,4-triazolinium hydroxide inner salt. Proof of structure was afforded by synthesis of 3-methyl-1-phenoxymethyl-4-phenyl-Δ²-1,2,4-triazoline-5-thione, 3-methyl-5-phenoxymethylthio-4-phenyl-1,2,4-triazole, and 2-methyl-2-phenoxymethyl-5-phenylimino-Δ³-1,3,4-thiadiazoline.