DIELS-ALDER REACTIONS OF ACYCLIC 2-AZADIENES - A SEMIEMPIRICAL MOLECULAR-ORBITAL STUDY

Authors
MELO TMVDPE FAUSTO R GONSALVES AMDR GILCHRIST TL
Citation
Tmvdpe. Melo et al., DIELS-ALDER REACTIONS OF ACYCLIC 2-AZADIENES - A SEMIEMPIRICAL MOLECULAR-ORBITAL STUDY, Journal of organic chemistry, 63(16), 1998, pp. 5350-5355
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
63
Issue
16
Year of publication
1998
Pages
5350 - 5355
Database
ISI
SICI code
0022-3263(1998)63:16<5350:DROA2->2.0.ZU;2-1
Abstract
Molecular orbital calculations (AM1) have been performed to obtain the frontier orbitals' (HOMO and LUMO) energies and polarization of a ser ies of acyclic 2-azadienes. The results are used to rationalize the re activity of the compounds studied with both electron-rich and electron -deficient dienophiles as well as the observed regioselectivity of the corresponding Diels-Alder reactions.