Theoretical Study of the Diels−Alder Reactions between Singlet (1Δg) Oxygen and Acenes
Citations Over TimeTop 10% of 2005 papers
Abstract
The G3(MP2) method has been employed to study the 1,4-addition reactions between singlet oxygen and five acenes, including benzene, naphthalene, anthrecene, tetracene, and pentacene. In all, nine pathways between O(2) and the five acenes have been investigated. Our calculated results indicate that all nine pathways are concerted and exothermic and that the most reactive sites on the acenes are the center ring's meso-carbons. In addition, reactivity increases along the series benzene < naphthalene < anthrecene < tetracene < pentacene. This trend is identical to that of aromaticity for the five acenes. A correlation between reactivity and aromaticity is briefly rationalized with natural bond orbital (NBO) analysis and frontier molecular orbital (FMO) analysis. Furthermore, some experimental kinetics data from the literature supporting the calculated results are cited.
Related Papers
- → Intramolecular Diels-Alder and Alder Ene Reactions(1984)192 cited
- → Diels-Alder reaction, inverse electronic demand Diels-Alder reaction, hetero-Diels-Alder reaction(2002)1 cited
- → Diels‐Alder and Hetero‐Diels–Alder Reactions(2013)11 cited
- → Consecutive Rh(I)‐Catalyzed Alder‐ene/Diels—Alder/Diels—Alder Reaction Sequence Affording Rapid Entry to Polycyclic Compounds.(2005)