Organoselenium Chemistry: Between Synthesis and Biochemistry

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The use of organoselenium reagents as catalysts is a common thread that runs through the chapters of this book, introducing important aspects of the modern organoselenium chemistry: organocatalysis, ...
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Selenoamides, Synthetic Methods and Recent Progress on their Synthetic Applications

Pp. 146-165 (20)

Toshiaki Murai

Abstract

This chapter has overviewed the stability of selenocarbonyl compounds that have been classified based on the substituents attached to their selenocarbonyl carbon atom. Focus has then been laid on the synthetic methods for selenoamides, whose chemistry has grown much more than that of other selenocarbonyl compounds in the last ten years. As starting materials leading to selenoamides, ordinary amides, nitriles and terminal acetylenes are mainly used. As a final part of this review, recent application of selenoamides to synthetic reactions has been introduced. Nucleophilic characters of selenium and nitrogen atoms in selenoamides have enabled several types of intermolecular cyclizations. The carbon atom of selenoamides can accept nucleophilic attack and selenium atom can formally work as a leaving group.

Keywords:

Selenocarbonyl compounds, Selenoamides, Amides, Nitriles, Acetylenes, Cyclization, Selenoiminium salts, Copper (0), Complexes, Photoinduction.

Affiliation:

Department of Chemistry, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-1193, Japan