The change of aromaticity along a Diels-Alder reaction path

被引:27
作者
Corminboeuf, C
Heine, T
Weber, J
机构
[1] Univ Geneva, Dept Phys Chem, CH-1211 Geneva 4, Switzerland
[2] Tech Univ Dresden, Inst Phys Chem & Elektrochem, D-01062 Dresden, Germany
关键词
D O I
10.1021/ol034203e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHIC] Quinodimethanes are highly reactive toward dienophiles since Diels-Alder cycloaddition results in an aromatic product. Density functional-based C-13, H-1 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.
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页码:1127 / 1130
页数:4
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