THE DEGRADATION OF CARBOXYLIC ACIDS INTO ALDEHYDES. REGIOSELECTIVE α-ACETOXYLATION OF 1,2,4-TRIAZOLIUM SALTS WITH DIACETOXYIODATE(1)ANION

Article abstract of DOI:10.1016/S0040-4020(01)83135-5

A novel method was developed for degradation of carboxylic acid into aldehydes containing one C atom less whose key step consists in α-acetoxylation of 5-alkyl-3-methylthio-1,4-diphenyl-1,2,4-triazolium iodides by (diacetoxyiodo)benzene.The mechanism of the regioselective α-acetoxylation was studied and the diacetoxy-iodate(1)anion was shown to be the actual oxidising agent.Further oxidation reactions of tetraethylammonium diacetoxyiodate(1) were investigated.A novel method was developed for the oxidation of primary alkyl amines into aldehydes by the novel heterocyclic reagent 5-bromo-3-methylthio-1,4-diphenyl-1,2,4-triazolium bromide and diethyl azodicarboxylate.