Kinetic and spectrophotometric investigation of the diels-alder reaction between maleic anhydride derivatives and substituted anthracenes in the presence of gallium and aluminum chlorides
A comparison was made of the kinetic data for the normal Diels-Alder reaction of para-substituted N-arylmaleimides and substituted maleic anhydrides with meso-substituted anthracenes and of the reaction catalyzed by gallium and aluminum chlorides. The largely constant effects of gallium chloride (10/sup 4/) and aluminum chloride (10/sup 5/) in the acceleration of the reactions between the various pairs were demonstrated. The energies of charge transfer in the complexes between hexamethylbenzene and the dienophiles in the presence and absence of Lewis acids were determined by spectrophotometry. A significant decrease (to 1.2 eV) of the charge-transfer energy was found in the ..pi.., ..pi..-complexes and was attributed to the stabilization of the LUMO of the dienophile. From analysis of the obtained data it was concluded that the observed catalytic effect in the presence of Lewis acids can be explained by the approach of the frontier orbital levels and by a favorable change in the coefficients at the atomic orbitals responsible for the reaction.
- Research Organization:
- Lenin Kazan State Univ.
- OSTI ID:
- 7170228
- Journal Information:
- J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 22:5,PT.2; ISSN JOCYA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400201* -- Chemical & Physicochemical Properties
ALUMINIUM CHLORIDES
ALUMINIUM COMPOUNDS
ANHYDRIDES
ANTHRACENE
AROMATICS
BENZENE
CARBOXYLIC ACIDS
CATALYSIS
CATALYTIC EFFECTS
CHEMICAL REACTION KINETICS
CHEMICAL REACTIONS
CHLORIDES
CHLORINE COMPOUNDS
CONDENSED AROMATICS
DICARBOXYLIC ACIDS
DIELS-ALDER REACTION
DIENES
DIOXANE
GALLIUM CHLORIDES
GALLIUM COMPOUNDS
HALIDES
HALOGEN COMPOUNDS
HETEROCYCLIC COMPOUNDS
HYDROCARBONS
HYDROGEN COMPOUNDS
INORGANIC ACIDS
KINETICS
LEWIS ACIDS
MALEIC ACID
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
POLYENES
REACTION KINETICS
SPECTROPHOTOMETRY