Unexpected thorpe reaction of an alpha-alkoxynitrile

Authors
Kovacs, L
Citation
L. Kovacs, Unexpected thorpe reaction of an alpha-alkoxynitrile, MOLECULES, 5(2), 2000, pp. 127-131
Citations number
15
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
MOLECULES
ISSN journal
14203049 → ACNP
Volume
5
Issue
2
Year of publication
2000
Pages
127 - 131
Database
ISI
SICI code
1420-3049(200002)5:2<127:UTROAA>2.0.ZU;2-V
Abstract
alpha-Alkoxynitrile 1 in the presence of tris(methylthio) methyllithium 2 a t -78 degrees C gave the dimer 5 instead of the expected Ci-elongated produ ct 3. The formation of compound 5 is explained in terms of anion formation and self-condensation, a variant of the Thorpe reaction. Scrutinizing the H -1 NMR spectra revealed that the enamine tautomer 5b is predominant over th e imine 5a in the solvents investigated.