1,3-dipolar cycloaddition reactions of stable bicyclic and monocyclic azomethine ylides: Kinetic aspects

Authors
Elender, K Riebel, P Weber, A Sauer, J
Citation
K. Elender et al., 1,3-dipolar cycloaddition reactions of stable bicyclic and monocyclic azomethine ylides: Kinetic aspects, TETRAHEDRON, 56(25), 2000, pp. 4261-4265
Citations number
18
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
25
Year of publication
2000
Pages
4261 - 4265
Database
ISI
SICI code
0040-4020(20000616)56:25<4261:1CROSB>2.0.ZU;2-U
Abstract
Kinetic data for 1,3-dipolar cycloadditions of stable azomethine ylides 1-3 with angle-strained, electron-poor and electron-rich 2 pi-components 4-10 prove that most reactions are LUMOdipole-HOMOdipolarophile-controlled. Smal l rho-values and a minor solvent effect on the rate constants are in accord with a concerted bond formation in the transition state. (C) 2000 Elsevier Science Ltd. All rights reserved.