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 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.