Computational Analysis on the Dual Reactivity of Conjugated “Ene-Ene-Yne” Systems

The design of new reactions that yield benzo-fused five- or six-membered rings arising from conjugated ene-ene-yne precursors was examined computationally. Inclusion of heteroatoms (particularly N) in the bond making position was shown to lower activation energies due to participation of the lone pa...

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Bibliographic Details
Published in:Journal of organic chemistry 2008-11, Vol.73 (22), p.8755-8762
Main Authors: McClintock, Sean P, Shirtcliff, Laura D, Herges, Rainer, Haley, Michael M
Format: Article
Language:English
Subjects:
Chemical reactivity
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Organic chemistry
Preparations and properties
Reactivity and mechanisms
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Summary:The design of new reactions that yield benzo-fused five- or six-membered rings arising from conjugated ene-ene-yne precursors was examined computationally. Inclusion of heteroatoms (particularly N) in the bond making position was shown to lower activation energies due to participation of the lone pair electrons in the cyclization reactions. By systematically varying the atomic configuration in the ene-ene-yne system, the influence of heteroatoms was used to identify optimal candidates for future experimental study.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo801390x