Theoretical approach to 1,3-dipolar cycloadditions involving fluorinated dipolarophiles

Authors
Naji, N Marakchi, K Kabbaj, OK Komiha, N Joffre, J Chraibi, M Soufiaoui, M
Citation
N. Naji et al., Theoretical approach to 1,3-dipolar cycloadditions involving fluorinated dipolarophiles, J FLUORINE, 94(2), 1999, pp. 127-133
Citations number
17
Categorie Soggetti
Inorganic & Nuclear Chemistry
Journal title
JOURNAL OF FLUORINE CHEMISTRY
ISSN journal
00221139 → ACNP
Volume
94
Issue
2
Year of publication
1999
Pages
127 - 133
Database
ISI
SICI code
0022-1139(19990405)94:2<127:TAT1CI>2.0.ZU;2-#
Abstract
Regioselectivity is studied in 1,3-dipolar cycloaddition involving fluorina ted dipolarophiles. Frontier orbitals from MNDO calculations of the optimiz ed structures are used. The results show a good agreement with experiment f or the nitrone and the diphenylnitrilimine. On the other hand, an inversion of regioselectivity is observed with the benzonitriloxide. The different s tructures of the dipolarophiles and the 1,3-dipoles have been optimized.