Catalytic aerobic oxidative cleavage of oximes, tosylhydrazones and N,N- dimethylhydrazones to carbonyl compounds

Synthesis

Volumn , Issue 3, 2000, Pages 403-406

  Blay, Gonzalo ^a   Benach, Elisabeth ^a   Fernández, Isabel ^a   Galletero, Sales ^a   Pedro, José R ^a   Ruiz, Rafael ^a  

^a UNIVERSITY OF VALENCIA   (Spain)

Author keywords

Hydrazone; Ketoxime; Metal catalyst; Ni(II) complex; Protective groups

Indexed keywords

CARBONYL DERIVATIVE; HYDRAZONE DERIVATIVE; NICKEL COMPLEX; OXIME DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; EPOXIDATION; OXIDATION; REACTION ANALYSIS;

EID: 0034007889     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2000-6347     Document Type: Article

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32. A similar effect on yields and rates was found when base was added to oxime cleavage reactions. However, in those reactions, hydroxylamine exchange in the absence of base was not observed and therefore the use of base was not required.
33. In the case of aliphatic N,N-dimethylhydrazones, the ketone is obtained by hydrazine exchange with pivalaldehyde and not by an oxidative process.
34. We have carried out the reaction on a 2 mmol scale and similar results were obtained if good stirring and good contact surface with oxygen is maintained.