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Theoretical investigation of mechanisms of thermal and photochemical reactions of 1,3,5-hexatriene and its structural and heterosubstituted analogs. III. Cyclization of 1-(3-phenyl)-1,3-butadiene to 1,8a-dihydronaphthalene

Journal Article · · J. Org. Chem. USSR (Engl. Transl.); (United States)
OSTI ID:5970485
; ;
The thermal cyclization and photocyclization of 1-(3-phenyl)-1,3-butadiene to 1,8a-dihydronaphthalene were investigated by the MINDO/3 method. The effect of annelation of 1,3,5-hexatriene on the barrier of the thermal reaction was investigated. It was shown that photocyclization takes place by a nonadiabatic path, and that the structure of the final product obeys the Woodward-Hoffman rules. Details of the reaction in the excited state were revealed: (1) The overcoming of a small activation barrier in the S/sub 1/ state (20 kJ/mole); (2) the transition to a minimum on the potential energy surface for the S/sub 1/ state; (3) subsequent nonradiative deactivation to the S/sub 0/ state by the contrary path. Photocyclization in the T/sub 1/ state does not take place on account of the high activation barrier (84 kJ/mole).
Research Organization:
M.A. Suslov Rostov State Univ. (USSR)
OSTI ID:
5970485
Journal Information:
J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 24:8; ISSN JOCYA
Country of Publication:
United States
Language:
English

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Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400500 -- Photochemistry
400800* -- Combustion
Pyrolysis
& High-Temperature Chemistry
657002 -- Theoretical & Mathematical Physics-- Classical & Quantum Mechanics
71 CLASSICAL AND QUANTUM MECHANICS
GENERAL PHYSICS
ACTIVATION ENERGY
AROMATICS
ATOMIC MODELS
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
COMPUTERIZED SIMULATION
CONDENSED AROMATICS
DEHYDROCYCLIZATION
DIENES
ELECTRONIC STRUCTURE
ENERGY
ENERGY GAP
ENERGY LEVELS
ENERGY-LEVEL TRANSITIONS
EXCITATION
EXCITED STATES
GROUND STATES
HYDROCARBONS
MATHEMATICAL MODELS
MECHANICS
MOLECULAR STRUCTURE
ORGANIC COMPOUNDS
PHOTOCHEMICAL REACTIONS
POLYENES
QUANTUM MECHANICS
SIMULATION
STRUCTURAL CHEMICAL ANALYSIS
THERMOCHEMICAL PROCESSES
YIELDS