Cyclones in the Diels-Alder reaction catalyzed by aluminum chloride
A comparison was made of the kinetic parameters for the uncatalyzed and catalyzed (with aluminum chloride) Diels-Alder reaction between N-arylmaleimides and acrylic, methacrylic, and fumaric esters as dienophiles and phencyclone and tetracyclone as dienes. By thermochemical and spectrophotometric experiments it was shown that the aluminum chloride coordinates with the dienophile in a ratio of 1:1. With a larger concentration of the catalyst coordination also takes place at the carbonyl of the diene. For the complexes of N-arylmaleimides the rate constants for the reaction with free tetracyclone and phencyclone increase by not more than 60 times, those for the esters of the unsaturated acids increase by 300-600 times, whereas those in the reaction with anthracene increase by 10/sup 5/ times. The results are discussed form the standpoint of the change in the energy of the molecular orbitals of the reagents.
- Research Organization:
- V.I. Ul'yanov-Lenin Kazan State Univ., USSR
- OSTI ID:
- 6035872
- Journal Information:
- J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 22:2; ISSN JOCYA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400201* -- Chemical & Physicochemical Properties
ACRYLIC ACID ESTERS
ALUMINIUM CHLORIDES
ALUMINIUM COMPOUNDS
ANTHRACENE
AROMATICS
ATOMIC MODELS
CARBOXYLIC ACID ESTERS
CARBOXYLIC ACIDS
CATALYSTS
CATALYTIC EFFECTS
CHEMICAL REACTION KINETICS
CHEMICAL REACTIONS
CHLORIDES
CHLORINE COMPOUNDS
COMPLEXOMETRY
CONDENSED AROMATICS
CONFIGURATION INTERACTION
COORDINATION NUMBER
DICARBOXYLIC ACIDS
DIELS-ALDER REACTION
DIENES
ELECTRONIC STRUCTURE
ENERGY LEVELS
ENERGY LOSSES
ENERGY-LEVEL TRANSITIONS
ESTERS
FUMARIC ACID
GALLIUM CHLORIDES
GALLIUM COMPOUNDS
HALIDES
HALOGEN COMPOUNDS
HYDROCARBONS
IMIDES
KINETICS
LOSSES
MATHEMATICAL MODELS
METHACRYLIC ACID
MONOCARBOXYLIC ACIDS
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
POLYENES
REACTION KINETICS
SPECTROPHOTOMETRY
THERMOCHEMICAL PROCESSES