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

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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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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Bicyclization of aza-compounds by positive halide ions. I. Cyclic amines

Canadian Journal of Chemistry ◽

10.1139/v85-199 ◽

1985 ◽

Vol 63 (6) ◽

pp. 1170-1172 ◽

Cited By ~ 6

Author(s):

R. M. Elofson ◽

F. F. Gadallah ◽

J. K. Laidler

Keyword(s):

Electrochemical Oxidation ◽

Halide Ions ◽

Cyclic Amine ◽

Reaction Conditions ◽

Specific Reaction ◽

Cyclic Amines ◽

Bicyclic Compounds

Cyclic amines are oxidized to the bicyclic compounds by electrochemical oxidation. The presence of halide ions is found necessary for the reaction to proceed and to produce any bicyclic products. It is postulated that a positive halide species, X(+), is produced electrochemically and stabilized under the specific reaction conditions. The X(+) ion forms a complex with the parent cyclic amine which decomposes to the bicyclic product and HX. An analogy between the Hofer–Moest reaction to produce C(+) and this reaction to produce X(+) is postulated

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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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