Anodic Oxidation of Benzil Hydrazones in the Presence of Halide Ions.

Mitsuhiro Okimoto; Yukio Takahashi

doi:10.1002/chin.200301092

Anodic Oxidation of Benzil Hydrazones in the Presence of Halide Ions.

ChemInform ◽

10.1002/chin.200301092 ◽

2003 ◽

Vol 34 (1) ◽

pp. no-no

Author(s):

Mitsuhiro Okimoto ◽

Yukio Takahashi

Keyword(s):

Anodic Oxidation ◽

Halide Ions

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Electrochemical Bifunctionalization of Olefins in the Presence of Halide Ions

Canadian Journal of Chemistry ◽

10.1139/v71-124 ◽

1971 ◽

Vol 49 (5) ◽

pp. 740-745 ◽

Cited By ~ 7

Author(s):

N. L. Weinberg ◽

A. Kentaro Hoffman

Keyword(s):

Anodic Oxidation ◽

Acetonitrile Solution ◽

Halide Ions ◽

Silver Salts ◽

Chemical Oxidants

An electrochemical procedure has been developed for halofunctionalization of olefins, which allows for introduction of both nitrogen and oxygen containing substituents. The method obviates the need for silver salts or chemical oxidants, presently employed in analogous chemical routes. Thus 1-phenyl-2-butene on electrolysis in acetonitrile solution containing Et4NI, Et4NBr, or Et4NCl was converted to the corresponding haloamide derivative. In a related study, which extends the scope of electrochemical functionalization by nitrogen to negatively substituted olefins, dimorpholinization of trans-dibenzoylethylene was carried out by anodic oxidation of an acetonitrile solution of the olefin in presence of morpholine and Et4NI.

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Bicyclization of aza-compounds by positive halide ions. II. Lactams and some related cyclizations

Canadian Journal of Chemistry ◽

10.1139/v87-460 ◽

1987 ◽

Vol 65 (12) ◽

pp. 2770-2773 ◽

Cited By ~ 8

Author(s):

Richard M. Elofson ◽

Fahmi F. Gadallah ◽

James K. Laidler

Keyword(s):

Anodic Oxidation ◽

Halide Ions ◽

Bicyclic Compounds ◽

Limited Success

Anodic oxidation of lactams in the presence of halide ions produced excellent yields of bicyclic compounds with reactants having rings in the range of eight to ten atoms (C7 to C9). Smaller rings did not react to form bicyclic products and larger rings gave reduced yields. Attempts were made to cyclize non-cyclic amides and to bicyclize cycloheptyl and cyclooctyl acetamide with limited success.

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