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A broadened scope for the use of hydrazones as neutral nucleophiles in the presence of H-bonding organocatalysts

 

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Opened Access A broadened scope for the use of hydrazones as neutral nucleophiles in the presence of H-bonding organocatalysts
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Author: Pettersen, Daniel
Perez Herrera, Raquel
Bernardi, Luca
Fini, Franscesco
Sgarzani, Valentina
Fernández Fernández, Rosario Fátima
Lassaletta Simón, José María
Ricci, Alfredo
Department: Universidad de Sevilla. Departamento de Química orgánica
Date: 2006
Published in: Synlett, 2, 239-242.
Document type: Article
Abstract: Using thioureas as H-bonding organocatalysts, nitroalkenes can be activated for the conjugate addition of hydrazones as neutral nucleophiles. Formaldehyde derivatives react at the azomethine carbon as expected, whereas hydrazones from enolizable aldehydes behave as ene-hydrazines and react at the α-carbon instead. Ionic liquids were found to decrease the reaction times considerably compared to commonly used solvents, whereas alternative activation by Lewis acids resulted in decomposition of reactants.
Cite: Pettersen, D., Perez Herrera, R., Bernardi, L., Fini, F., Sgarzani, V., Fernández, R.,...,Ricci, A. (2006). A broadened scope for the use of hydrazones as neutral nucleophiles in the presence of H-bonding organocatalysts. Synlett, 2, 239-242.
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URI: https://hdl.handle.net/11441/70294

DOI: 10.1055/s-2005-922791

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