Review article

On the Chemistry of Stable α-Oxoketenes

Gert Kollenz ; Institute of Chemistry, Organic and Bioorganic Division, KF-University of Graz, A-8010 Graz, Austria
Werner Heilmayer ; Institute of Chemistry, Organic and Bioorganic Division, KF-University of Graz, A-8010 Graz, Austria
C. Oliver Kappe ; Institute of Chemistry, Organic and Bioorganic Division, KF-University of Graz, A-8010 Graz, Austria
Bianca Wallfisch ; Institute of Chemistry, Organic and Bioorganic Division, KF-University of Graz, A-8010 Graz, Austria
Curt Wentrup ; Department of Chemistry, The University of Queensland, Brishane, Qu-4072, Australia

Abstract

This short review describes the preparation and Chemistry of sterically stabilized α-oxoketenes, which can be isolated and handled as true neat compounds. Their reactions with dienophiles afford [4+2] - as well as [2+2] cycloadducts depending on their ability to adopt that conformation suitable for each type of cycloaddition reactions. Addition of nucleophiles leads either to dipivaloylacetic acid derivatives as expected products or to the rare molecular skeleton of mono- or bifunctionalized bridged bisdioxines, which exhibit axial chirality. The bifunctionalized derivatives may serve as novel spacer units in several macrocyclic systems.

Keywords

α -oxoketenes; preparation and Chemistry; cycloaddition reactions; addition of nucleophiles; bridged bisdioxines; macro-cycles

Hrčak ID:

131957

URI

https://hrcak.srce.hr/131957

Publication date:

1.11.2001.

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