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Synlett 1991; 1991(11): 787-788
DOI: 10.1055/s-1991-20875
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Silica Gel Catalyzed Eschenmoser Reaction

Antonio Abad* , Consuelo Agulló, Manuel Arnó, Ana C. Cuñat, Ramón J. Zaragozá
  • *Departamento de Química Orgánica, Facultad de Químicas, Universidad de Valencia, Dr. Moliner 50, E-46100 Burjassot, Valencia, Spain
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Publication Date:
07 March 2002 (online)

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Silica gel has been shown to be an effective catalyst for the ring opening of α,β-epoxycycloalkanones with p-toluene-sulfonohydrazide (the Eschenmoser reaction). The reaction conditions are extremely mild and excellent yields of acetylenic-carbonyl compounds (6-heptyn-2-ones and 2-(3-butynyl)-cycloalkanones) are obtained even with unreactive substrates.