Spontaneous Aerobic Oxidation of 1,1,2,2-Tetrakis(N-methylpyridin- 4-ium)ethane Iodide to the Alkene and the Epoxide.

The tetrapyridinium salt 1 was found to undergo quantitative air oxidation upon dissolving it in water. The corresponding alkene and the epoxide were found as the only products of the oxidation. A mechanism that involves an alkyl hydroperoxide intermediate 1″ undergoing a transformation that yields both products is proposed. Air oxidation of 1 shows the potential of the acceptor substituted alkanes to be used in the studies of mostly unknown direct epoxidation of single C-C bonds.