Design of Unusual Captodative Methylene Substrates: 1-Alkyl-4(3)-(azolylmethyl)pyridinium Salts

Article abstract of DOI:10.1016/0040-4020(95)00850-8

The unprecedented spontaneous oxidation of a carbon atom linked to captor (acceptor) and donor non-classical functional groups of several examples of 1-alkyl-4(3)-(1H-azolylmethyl)pyridinium salts 1 and 2 exemplifies a concomitant application of the areno-analogy principle and the captodative effect in organic synthesis.A remarkably driving force by the nature of non-classical acceptor and donor heteroaromatic rings is observed upon the chemical behavior of the title compounds 1 and 2, modulating the susceptibility with which the methylene spacers oxidize to their oxomethyl counterparts 5 and 6.Access to dipolar 1-alkyl-3-pyridiniomethyl-3(5)-1,2,4-triazolate inner salts 4 was achieved.