Next Article in Journal
1,3-Dipolar Cycloadditions of N-Benzyl Furfuryl Nitrones with Electron-rich Alkenes
Previous Article in Journal
NaY Zeolite: A Useful Catalyst for Nitrile Hydrolysis
Molecules 2000, 5(2), 127-131; doi:10.3390/50200127
Article

Unexpected Thorpe Reaction of an α-Alkoxynitrile

Department of Medicinal Chemistry, University of Szeged, Dóm tér 8., H-6720 Szeged, Hungary
Received: 19 January 2000 / Accepted: 14 February 2000 / Published: 17 February 2000
Download PDF [26 KB, uploaded 18 June 2014]
SciFeed

Abstract

α-Alkoxynitrile 1 in the presence of tris(methylthio)methyllithium 2 at –78ºC 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.
Keywords: Thorpe reaction; self-condensation Thorpe reaction; self-condensation
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote |
RIS
MDPI and ACS Style

Kovács, L. Unexpected Thorpe Reaction of an α-Alkoxynitrile. Molecules 2000, 5, 127-131.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert