Redox behavior of active aldehydes derived from thiamin coenzyme analogs

Redox behavior of active aldehydes of thiamin coenzyme models has been investigated using 3-benzylthiazolium salts and o-tolualdehyde in the presence of a base. The use of a sterically hindered aldehyde has precluded benzoin condensation of the active aldehydes, leading to the formation of relatively stable active aldehydes. The redox potentials of the active aldehydes have been determined by cyclic voltammetry for the first time, and they are sufficiently negative to reduce C-60 to the corresponding dianion (C-60(2-)).