Product, Radical Intermediates, and Hydrogen Atom Production in the Thermal Decomposition of 1,2-Dihydronaphthalene

Article abstract of DOI:10.1021/jo00193a022

The thermal decomposition of 1,2-dihydronaphthalene (DHN) at 300 deg C produces tetralin, naphthalene, hydrogen and five C20 hydrocarbon products (1-5).The isolation of compounds 1-5 from the thermal decomposition of 1,2-dihydronaphthalene-4-d revealed compounds 1 and 2 to be formed by the addition of 2-hydronaphtyl (2HN) to DHN followed by intramolecular cyclization and hydrogen abstraction.Compound 3 was formed by addition of 1-tetralyl radical to DHN followed by hydrogen abstraction, and compounds 4 and 5 were formed by a sequence involving initial addition of 2-tetralyl radical to dihydronaphthalene.The thermal decomposition of DHN at 400-450 deg C leads to the formation of a hydrogen atom which participates in subsequent hydrocracking reactions of available substituted aromatic structures.