TRANSITIONS OF ELECTRON DEMAND IN PERICYCLIC-REACTIONS - NORMAL, NEUTRAL, AND INVERSE DIELS-ALDER REACTIONS OF POLYHALOGENATED CYCLOPENTADIENES

Authors
EIBLER E HOCHT P PRANTL B ROSSMAIER H SCHUHBAUER HM WIEST H SAUER J
Citation
E. Eibler et al., TRANSITIONS OF ELECTRON DEMAND IN PERICYCLIC-REACTIONS - NORMAL, NEUTRAL, AND INVERSE DIELS-ALDER REACTIONS OF POLYHALOGENATED CYCLOPENTADIENES, Liebigs Annalen, (12), 1997, pp. 2471-2484
Citations number
81
Journal title
Liebigs Annalen → ACNP
ISSN journal
09473440
Issue
12
Year of publication
1997
Pages
2471 - 2484
Database
ISI
SICI code
0947-3440(1997):12<2471:TOEDIP>2.0.ZU;2-C
Abstract
Normal, neutral, and inverse-type Diels-Alder reactions can be observe d in [4+2] cycloadditions of polyhalogenated cyclopentadienes 1a-1i wi th various aryl-substituted cyclic and open-chain dienophiles, and cha racteristic gradations of reactivity associated with the different mec hanistic types are often displayed. Reaction rate constants and semiem pirically derived HOMO and LUMO values for the reactants suggest that neutral [4+2] cycloadditions should be regarded as a transition betwee n normal and inverse Diels-Alder reactions.