Download PDF
Synlett 1991; 1991(3): 189-190
DOI: 10.1055/s-1991-20674
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

A Convenient Mild Two-Step Conversion of Imines to Secondary and Tertiary Amides

R. Alan Aitken* , Swati V. Raut
  • *Department of Chemistry, University of St. Andrews, North Haugh, St. Andrews, Fife, KY16 9ST, Scotland
Further Information

Publication History

Publication Date:
07 March 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

Treatment of Δ2-1,2,4-oxadiazolines (4,5-dihydro-1,2,4-oxadiazoles), readily formed by cycloaddition of nitrite oxides to imines, with potassium tert-butoxide leads to cycloreversion of the resulting anions to give a nitrite and the amide anion which can be hydrolysed or alkylated to provide a mild nonoxidising method for the synthesis of secondary or tertiary amides. Deprotonation of the 1,4,2-dioxazoles available from aromatic aldehydes and nitrite oxides similarly affords carboxylic acids and methyl esters.