Citation
Mj. Walker et al., Torquoselectivity induced by lone-pair conjugation in the electrocyclic reactions of 1-azapolyenes, J ORG CHEM, 66(20), 2001, pp. 6669-6672
Citations number
65
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263
→ ACNP
Volume
66
Issue
20
Year of publication
2001
Pages
6669 - 6672
Database
ISI
SICI code
0022-3263(20011005)66:20<6669:TIBLCI>2.0.ZU;2-Z
Abstract
Torquoselectivity in the electrocyclic interconversions of 1-azapolyenes. a
nd their heterocyclic isomers was investigated theoretically. The ring open
ings of 1,2-dihydroazete, 1,2-dihydropyridine, and 1,2-dihydroazocine were
examined using HF, MP2, and B3LYP calculations. A large preference for inwa
rd rotation of the nitrogen lone pair and outward rotation of the N-H group
was found for the four- and six-electron. systems. No strong preference wa
s observed for the eight-electron system.