Synthesis and Reactions of 1,3,5-Tri- and 1,3,5,7-Tetracarbonyl Compounds

Peter Langer

doi:10.1055/s-0037-1610780

Synlett, Table of Contents

Synlett 2021; 32(20): 2036-2045
DOI: 10.1055/s-0037-1610780

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Synthesis and Reactions of 1,3,5-Tri- and 1,3,5,7-Tetracarbonyl Compounds

Peter Langer ∗

^aInstitut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany

^bLeibniz-Institut für Katalyse an der Universität Rostock e. V., Albert-Einstein-Str. 29a, 18059 Rostock, Germany

› Author Affiliations

Abstract

All articles of this category

Dedicated to Mrs. Adelgunde Fifelski on the occasion of her birthday.

Abstract

The reaction of 1,3-bis(silyloxy)-1,3-butadienes with functionalized and nonfunctionalized acid chlorides and bis(acid chlorides) gives rise to the formation of a great variety of 1,3,5-tri- and 1,3,5,7-tetracarbonyl compounds and cyclic products derived from them. Examples include functionalized and nonfunctionalized 3,5-dioxopentanoates, 3,5-dioxopimelates, 3-alkylidene-3H-isobenzofuran-1-ones, salicylates, 3(2H)furanones, and 3-oxo-4-sulfonylesters. Methylation and cyclopropanation reactions of 1,3,5-tri- and 1,3,5,7-tetracarbonyl compounds do not provide access to the expected permethylated and cyclopropanated polycarbonyl compounds. However, the latter could be prepared by stepwise protocols. The reaction of 1,3,5-tri- and 1,3,5,7-tetracarbonyl compounds with dinucleophiles resulted in cyclization reactions to give a variety of heterocyclic structures.

1 Introduction

2 Reactions of 1,3-Bis(silyloxy)-1,3-butadienes with Acid Chlorides

3 Reactions of 1,3,5-Tri- and 1,3,5,7-Tetracarbonyl Compounds

4 Conclusion

Keywords

carbonyl compounds - condensation reactions - cyclopropanes - heterocycles - silyl enol ethers

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References

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