Unconventional acceptor and donor functional groups linked by a captodative spacer

Article abstract of DOI:10.1016/S0040-4020(96)00968-4

The chemical stability to oxidation of a set of compounds built up from acceptor and donor subunits linked by a methylene or a hydroxymethylene group was studied. Whereas 1-butyl-3-[1,2,4-triazol-5(3)-ylmethyl]pyridinium salts 2d,e showed high stability to oxidation, 1-butyl-4-[imidazol-4(5)-ylhidroxymethyl]pyridinium salt 14f was oxidised spontaneously to the corresponding carbonyl compound, indicating the capability of the oxidation phenomenon to be controlled by the nature of the building blocks.