Abstract
Cyclic oxonitriles exhibit unusual regio- and chemoselectivities, reflecting the juxtaposition of electron-withdrawing ketone and nitrile functionalities. In this review, synthetic access to β- and γ-oxonitriles is surveyed, as are the reactions of these two classes of oxonitriles. Collectively, the synopsis aims to highlight the synergistic properties of the nitrile and ketone groups by emphasizing synthetic applications which are otherwise difficult or impossible to perform.
1 Introduction
2 Physical Properties
2.1 β-Oxonitrile Syntheses
2.2 γ-Oxonitrile Syntheses
2.3 β-Oxoalkenenitrile Syntheses
2.4 γ-Oxoalkenenitrile Syntheses
3 Reactions of Oxonitriles
3.1 Alkylations of β-Oxonitriles
3.2 Alkylations of γ-Oxonitriles
3.3 Michael Additions of β-Oxonitriles
3.4 Michael Additions of γ-Oxonitriles
3.5 Reduction and Nucleophilic Additions to β-Oxonitriles
3.6 Reduction and Nucleophilic Additions to γ-Oxoalkenenitriles
3.7 Conjugate Additions to β-Oxoalkenenitriles
3.8 Ring Contraction, Cleavage, and Expansion of β-Oxonitriles
3.9 Ring Cleavage of γ-Oxonitriles
3.10 Cycloadditions with β-Oxoalkenenitriles
3.11 Cycloadditions with γ-Oxoalkenenitriles
3.12 Miscellaneous Reactions
4 Future Directions
Key words
oxonitriles - nitriles - alkylations - cyclizations - synthesis
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