The thermal decomposition of 2,2′-azobis(2-methylpropionitrile) in the presence of 2,6-Di-t-butyl and 2,6-diphenyl-1,4-benzoquinone

The thermal decomposition of 2,2′-azobis(2-methylpropionitrile) in the presence of 2,6-di-t-butyl-1,4-benzoquinone results in the formation of 2,6-di-t-butyl-1,4-di(2-cyano-2-propoxy)benzene as the only addition product, whereas the thermal decomposition of the azo compound in the presence of 2,6-diphenyl-1,4,benzoquinone gives rise to the formation of the corresponding diether (major product), together with smaller amounts of both possible monoethers. 2,5-Di-t-butyl-1,4-benzoquinone failed to give any addition products, in agreement with earlier reports. Possible mechanisms are discussed.