CYCLOADDITIONS: X. KINETICS OF THE THERMAL DECARBONYLATION OF DICYCLOPENTADIENE-1.8-DIONE
Open Access
- 1 September 1966
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 44 (17), 2051-2056
- https://doi.org/10.1139/v66-305
Abstract
The thermal cycloelimination of carbon monoxide from dicyclopentadiene-1,8-dione is a kinetically well-behaved first-order reaction. At 380 °K the activation parameters for the process are ΔH≠ = 34.5 ± 0.8 kcal mole−1 and ΔS≠ = +9.8 ± 2.3 e.u. mole−1. Application of the theoretical proposals of Woodward and Hoffmann indicates that this necessarily disrotatory decarbonylation may be concerted.Keywords
This publication has 21 references indexed in Scilit:
- Dienes from 3-Pyrrolines. A Stereospecific DeaminationJournal of the American Chemical Society, 1966
- 7-Azabenzonorbornadiene1The Journal of Organic Chemistry, 1966
- 2,3-Diphenylvinylene SulfoneJournal of the American Chemical Society, 1965
- Formation of Desoxybenzoin in the Borohydride Reduction of the Reaction Mixture of Benzoin with Thionyl Chloride and Pyridine*The Journal of Organic Chemistry, 1965
- On the chlorination of dicyclopentadiene-1,8-dioneTetrahedron Letters, 1963
- Carbonyl Bridge Compounds.Chemical Reviews, 1962
- Zur Kenntnis des CyclopentadienonsEuropean Journal of Inorganic Chemistry, 1961
- Cyclopentene-3,5-dione. II. Conversion to CyclopentadienoneJournal of the American Chemical Society, 1960
- The mechanism of the Diels-Alder reactionTetrahedron, 1959
- Preparation and Physical Properties of Sulfur Compounds Related to Petroleum. VII. 2-, 6- and 8-Thiabicyclo[3.2.1]octane and 2-Thiabicyclo[2.2.2]octaneThe Journal of Organic Chemistry, 1957