Synthesis of the covalent benzene-carbon monoxide cycloadduct, norborna-2,5-dien-7-one. Correlation of kinetic and thermodynamic stabilities in cycloreversion reactions

David M. Birney, Jerome A. Berson

Research output: Contribution to journalArticlepeer-review

34 Scopus citations

Abstract

endo-Tricyclo[4.2.1.02,5]non-7-ene-3,4,9-trione (14) is prepared from the 5,5-diethoxy-cyclopcntadiene-diethyl maleate Diels-Alder adduct. Photolysis of the trione in CD2Cl2 solution at 192 K forms norborna-2,5-dien-7-one (2). The latter substance is thermally unstable and decomposes to benzene and CO with ΔG‡ =15 kcal mol-1. This appears to be the lowest activation energy for a cycloreversion yet measured. A correlation is found for the kinetic and thermodynamic stabilities in a series of 18 orbital symmetry allowed cycloreversions by plotting ΔG‡ vs ΔHr.

Original languageEnglish
Pages (from-to)1561-1570
Number of pages10
JournalTetrahedron
Volume42
Issue number6
DOIs
StatePublished - 1986

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