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

Autor: Tcyrulnikov, Nikolai A., Tikhomirova, Anastasiia A., Tcyrulnikov, Sergei, Wilson, R. Marshall
Zdroj: Organic Letters; 20240101, Issue: Preprints
Abstrakt: The tetrapyridinium salt 1was 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 1shows the potential of the acceptor substituted alkanes to be used in the studies of mostly unknown direct epoxidation of single C–C bonds.
Databáze: Supplemental Index