Eschenmoser fragmentation

What is Eschenmoser fragmentation?

The Eschenmoser fragmentation, also referred to as the Eschenmoser-Tanabe fragmentation, is a chemical reaction that involves the mild cleavage of α,β-epoxyketones through sulfonylhydrazone intermediates, resulting in the formation of acetylenic and carbonyl compounds.

Eschenmoser fragmentation
Eschenmoser fragmentation

References

  • Eschenmoser, A., Felix, D. and Ohloff, G. (1967), Eine neuartige Fragmentierung cyclischer α, ß-ungesättigter Carbonylsysteme; Synthese von Exalton und rac-Muscon aus Cyclododecanon Vorläufige Mitteilung. [A novel fragmentation of cyclic α, ß-unsaturated carbonyl systems; synthesis of exaltone and rac-muscone from cyclododecanone Preliminary communication.] Helvetica Chimica Acta, 50: 708-713. https://doi.org/10.1002/hlca.19670500232
  • Schreiber, J., Felix, D., Eschenmoser, A., Winter, M., Gautschi, F., Schulte-Elte, K.H., Sundt, E., Ohloff, G., Kalovoda, J., Kaufmann, H., Wieland, P. and Anner, G. (1967), Die Synthese von Acetylen-carbonyl-Verbindungen durch Fragmentierung von α, β-Epoxy-ketonen mit p-Toluolsulfonylhydrazin. Vorläufige Mitteilung. [The synthesis of acetylene-carbonyl compounds by fragmentation of α,β-epoxy-ketones with p-toluenesulfonylhydrazine. Preliminary communication.] Helvetica Chimica Acta, 50: 2101-2108. https://doi.org/10.1002/hlca.19670500747
  • Masato Tanabe, David F. Crowe, Robert L. Dehn, A novel fragmentation reaction of α,β-epoxyketones the synthesis of acetylenic ketones, Tetrahedron Letters 8 (40) 3943-3946,
    DOI: 10.1016/S0040-4039(01)89757-4.
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