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The Change of Aromaticity along a Diels−Alder Reaction Path

2003; American Chemical Society; Volume: 5; Issue: 7 Linguagem: Inglês

10.1021/ol034203e

1523-7060

Clémence Corminbœuf, Thomas Heine, Jacques Weber,

Photochemistry and Electron Transfer Studies

[reaction: see text] Quinodimethanes are highly reactive toward dienophiles since Diels-Alder cycloaddition results in an aromatic product. Density functional-based (13)C, (1)H NMR, NICS, and MO-NICS calculations indicate that the increase of aromatic character of the developing benzenoid ring along the reaction path is especially pronounced after the transition state is reached, even though the number of pi orbitals decreases. The forming aliphatic ring exhibits large ring current effects during the reaction.