HOMOALLYL CYANIDE AND N-ALLYLKETENE IMINE - A [3,3]SIGMATROPIC EQUILIBRIUM

Authors
BRUCKNER R HUISGEN R
Citation
R. Bruckner et R. Huisgen, HOMOALLYL CYANIDE AND N-ALLYLKETENE IMINE - A [3,3]SIGMATROPIC EQUILIBRIUM, Tetrahedron letters, 35(20), 1994, pp. 3281-3284
Citations number
12
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
20
Year of publication
1994
Pages
3281 - 3284
Database
ISI
SICI code
0040-4039(1994)35:20<3281:HCANI->2.0.ZU;2-3
Abstract
The [sic],delta-unsaturated nitrile 2 equilibrates at room temperature with the N-allylketene imine 3. Deuterium labeling established an int ramolecular rearrangement, and the small influence of solvent polarity on the rare constants is in accordance with a concerted [3,3]sigmatro pic shift.