Crown cation complex effects. 10. Potassium tert-Butoxide mediated penultimate oxidative hydrolysis of nitriles

SA DiBiase, RP Wolak Jr, DM Dishong…

Index: DiBiase, Stephen A.; Wolak, Raymond P.; Dishong, Dennis M.; Gokel, George W. Journal of Organic Chemistry, 1980 , vol. 45, # 18 p. 3630 - 3634

Full Text: HTML

Citation Number: 40

Abstract

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 21-93% and are found to be highest for long- ...

Related Articles:

Ruthenium-catalyzed oxidative cleavage of alkynes to carboxylic acids

[Yang, Dan; Chen, Fei; Dong, Ze-Min; Zhang, Dan-Wei Journal of Organic Chemistry, 2004 , vol. 69, # 6 p. 2221 - 2223]

Fast and selective oxidation of primary alcohols to aldehydes or to carboxylic acids and of secondary alcohols to ketones mediated by oxoammonium salts under two- …

[Anelli, Pier Lucio; Biffi, Carlo; Montanari, Fernando; Quici, Silvio Journal of Organic Chemistry, 1987 , vol. 52, # 12 p. 2559 - 2562]

Osmium tetroxide-promoted catalytic oxidative cleavage of olefins: an organometallic ozonolysis

[Travis, Benjamin R.; Narayan, Radha S.; Borhan, Babak Journal of the American Chemical Society, 2002 , vol. 124, # 15 p. 3824 - 3825]

Fast catalytic epoxidation with H2O2 and [γ-SiW10O36 (PhPO) 2] 4-in ionic liquids under microwave irradiation

[Carraro, Mauro; Sandei, Luca; Sartorel, Andrea; Scorrano, Gianfranco; Bonchio, Marcella Organic Letters, 2006 , vol. 8, # 17 p. 3671 - 3674]

Highly selective hydrogenation of multiple carbon–carbon bonds promoted by nickel (0) nanoparticles

[Alonso, Francisco; Osante, Inaki; Yus, Miguel Tetrahedron, 2007 , vol. 63, # 1 p. 93 - 102]

More Articles...