Crown Cation Complex Effects. 10. Potassium tert-Butoxide Mediated Penultimate Oxidative Hydrolysis of Nitriles

Article abstract of DOI:10.1021/jo01306a018

The failure of phase-transfer catalysis to improve either the yield or rapidity of basic nitrile hydrolysis is due, in part, to the poor solubility of quaternary ammonium hydroxides in nonpolar solutions.An alternative hydrolysis method which involves potassium tert-butoxide mediated oxidative cleavage of the nitrile with loss of the cyano carbon is presented.The isolated yields reported here range from 21-93percent and are found to be highest for long-chain aliphatic nitriles such as cyanohexadecane.