1,3-DIPOLAR CYCLOADDITION OF PHENYL AZIDE TO NORBORNENE IN AQUEOUS-SOLUTIONS

Authors
WIJNEN JW STEINER RA ENGBERTS JBFN
Citation
Jw. Wijnen et al., 1,3-DIPOLAR CYCLOADDITION OF PHENYL AZIDE TO NORBORNENE IN AQUEOUS-SOLUTIONS, Tetrahedron letters, 36(30), 1995, pp. 5389-5392
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
30
Year of publication
1995
Pages
5389 - 5392
Database
ISI
SICI code
0040-4039(1995)36:30<5389:1COPAT>2.0.ZU;2-8
Abstract
Second-order rate constants for the cycloaddition of phenyl azide to n orbornene were determined in aqueous solutions. In organic solvents th is reaction shows a very small solvent effect. In highly aqueous media , however, remarkable accelerations are observed. The solvent dependen ce of the rate constants on solvent composition in mixed aqueous solut ions resembles those observed for Diels-Alder reactions, most likely b ecause both types of cycloadditions are mechanistically related.