Reaction of nitrones with silyl ketene acetals: A DFT study

✍ Scribed by Anne Milet; Yves Gimbert; Andrew E. Greene

• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: English
• Weight: 389 KB
• Volume: 27
• Category: Article
• ISSN: 0192-8651
• DOI: 10.1002/jcc.20322

✦ Synopsis

Abstract

Theoretical calculations at the DFT level indicate that the reaction of a nitrone with a silyl ketene acetal proceeds, contrary to previous suggestions, through a classical 1,3‐dipolar cycloaddition, followed by a silyl group transfer step to give the open‐chain product. Introduction of a diffuse basis set is necessary to describe properly nitrones. The influence of a Lewis acid has been studied. © 2005 Wiley Periodicals, Inc. J Comput Chem 27: 157–162, 2006