Bulletin of the Chemical Society of Japan

Mechanism of the reaction of nitriles with alkaline hydrogen peroxide. Reactivity of peroxycarboximidic acid and application to superoxide ion reaction.

Y Sawaki, Y Ogata

Index: Sawaki, Yasuhiko; Ogata, Yoshiro Bulletin of the Chemical Society of Japan, 1981 , vol. 54, # 3 p. 793 - 799

Full Text: HTML

Citation Number: 51

Abstract

Formation of peroxycarboximidic acid (1) is not rate-determining in the reaction of nitrile with alkaline hydrogen peroxide to form amide and oxygen; the yield of amide based on H 2 O 2 varies from 20 to 60%. When dimethyl sulfoxide (DMSO), a reactive substrate, is added, the rate is independent of DMSO and governed in turn by a rate-determining addition of HOO− to nitrile. This reaction gives a reliable α-value of k HOO−/k HO−, which is 10000 for ...

Related Articles:

Cyclopalladated ferrocenylimines: highly active catalysts for Heck reactions

[Wu, Yangjie; Hou, Jianjun; Yun, Hongying; Cui, Xiuling; Yuan, Ruijuan Journal of Organometallic Chemistry, 2001 , vol. 637-639, p. 793 - 795]

Rh-Catalyzed one-pot and practical transformation of aldoximes to amides

[Park, Soyoung; Choi, Yoon-aa; Han, Hoon; Yang, Soon Ha; Chang, Sukbok Chemical Communications, 2003 , # 15 p. 1936 - 1937]

Efficient synthesis of primary amides using 2-mercaptopyridone-1-oxide-based uronium salts

[Bailen; Chinchilla; Dodsworth; Najera Tetrahedron Letters, 2000 , vol. 41, # 50 p. 9809 - 9813]

Binaphthyl-bridged bis-imidazolinium salts as N-heterocyclic carbene ligand precursors in the palladium-catalyzed Heck reaction

[Wu, Hui; Jin, Can; Huang, Guoli; Wang, Lianjun; Jiang, Juli; Wang, Leyong Science China Chemistry, 2011 , vol. 54, # 6 p. 951 - 956]

A One??Pot Synthesis of Primary Amides from Aldoximes or Aldehydes in Water in the Presence of a Supported Rhodium Catalyst

[Angewandte Chemie - International Edition, , vol. 46, # 27 p. 5202 - 5205]

More Articles...