Alkene epoxidations catalyzed by iron(III), manganese(III), and chromium(III) porphyrins. Effects of metal and porphyrin substituents on selectivity and regiochemistry of epoxidation
Journal Article
·
· Journal of the American Chemical Society; (USA)
- Univ. of California, San Diego (USA)
The products of epoxidation of norbornene, cyclohexene, and adamantylideneadamantane with pentafluoroiodobenzene using as catalysts variously substituted tetraphenylporphyrin complexes of chloroiron (III), chloromanganese(III), and chlorochromium(III) have been determined. All catalysts afforded the epoxide from adamantylideneadamantane, suggesting that the metallacycle intermediate, impossible in this case, is not required for epoxidation. The electronegatively substituted iron porphyrins show a great tendency toward epoxidation rather than allylic oxidation and show more selectivity for cis-alkenes.
- OSTI ID:
- 6725440
- Journal Information:
- Journal of the American Chemical Society; (USA), Journal Name: Journal of the American Chemical Society; (USA) Vol. 111:19; ISSN 0002-7863; ISSN JACSA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
36 MATERIALS SCIENCE
360104 -- Metals & Alloys-- Physical Properties
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400200* -- Inorganic
Organic
& Physical Chemistry
ALKENES
CALCULATION METHODS
CARBOXYLIC ACIDS
CATALYSTS
CHEMICAL REACTIONS
CHROMIUM
DATA
DATA ANALYSIS
ELEMENTS
EPOXIDES
EXPERIMENTAL DATA
HETEROCYCLIC ACIDS
HETEROCYCLIC COMPOUNDS
HYDROCARBONS
INFORMATION
IRON
MANGANESE
MEASURING INSTRUMENTS
MEASURING METHODS
METALS
NUMERICAL DATA
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
PORPHYRINS
TRANSITION ELEMENTS
360104 -- Metals & Alloys-- Physical Properties
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400200* -- Inorganic
Organic
& Physical Chemistry
ALKENES
CALCULATION METHODS
CARBOXYLIC ACIDS
CATALYSTS
CHEMICAL REACTIONS
CHROMIUM
DATA
DATA ANALYSIS
ELEMENTS
EPOXIDES
EXPERIMENTAL DATA
HETEROCYCLIC ACIDS
HETEROCYCLIC COMPOUNDS
HYDROCARBONS
INFORMATION
IRON
MANGANESE
MEASURING INSTRUMENTS
MEASURING METHODS
METALS
NUMERICAL DATA
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
PORPHYRINS
TRANSITION ELEMENTS