Bimolecular reactions of 3-methylene-1,4-cyclohexadiene (p-isotoluene), 5-methylene-1,3-cyclohexadiene (o-isotoluene), 1-methylene-1,4-dihydronaphthalene (benzo-p-isotoluene), and 9-methylene-9,10-dihydroanthracene (dibenzo-p-isotoluene)

Autor:	Joseph J. Gajewski, Andrea M. Gortva
Rok vydání:	1989
Předmět:	Chemical kinetics chemistry.chemical_compound Anthracene chemistry Organic Chemistry Methylene 9 10-Dihydroanthracene 1 3-Cyclohexadiene Photochemistry Chemical reaction Isotoluene Ene reaction
Zdroj:	The Journal of Organic Chemistry. 54:373-378
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo00263a021
Popis:	3-Methylene-1,4-cyclohexadiene, 1,5-methylene-1,3-cyclohexadiene, 2, 1-methylene-1,4-dihydronaphthalene, 5, and 9-methylene-9,10-dihydroanthracene, 8, react with second-order kinetics in benzene solution. The activation parameters for the reaction of 1, 5, and 8, especially the frequency factor, suggest a nonconcerted reaction with little orientational demand in the transition state. The frequency factor for the reaction of 2 suggests a concerted pathway. The product distribution from each compound reinforces the kinetic observations. The products from the pyrolysis of 1 could be rationalized by a radical cage intermediate, which could combine or disproportionate. The reaction products from 5 indicate a radical chain oligomerization. The reaction of 8 gives an insoluble solid. o-Isotoluene (2) gives ene dimers. 18 references.
Databáze:	OpenAIRE
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