Unexpected thorpe reaction of an α-alkoxynitrile

Research output: Article

3 Citations (Scopus)

Abstract

α-Alkoxynitrile 1 in the presence of tris(methylthio)methyllithium 2 at -78°C gave the dimer 5 instead of the expected C1(-elongated product 3. The formation of compound 5 is explained in terms of anion formation and self-condensation, a variant of the Thorpe reaction. Scrutinizing the 1H NMR spectra revealed that the enamine tautomer 5b is predominant over the imine 5a in the solvents investigated.

Original languageEnglish
Pages (from-to)127-131
Number of pages5
JournalMolecules
Volume5
Issue number2
Publication statusPublished - febr. 2000

Fingerprint

Imines
Dimers
Anions
Condensation
Nuclear magnetic resonance
tautomers
imines
condensation
dimers
anions
nuclear magnetic resonance
products
methyllithium
Proton Magnetic Resonance Spectroscopy

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Unexpected thorpe reaction of an α-alkoxynitrile. / Kovács, L.

In: Molecules, Vol. 5, No. 2, 02.2000, p. 127-131.

Research output: Article

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