Article
A broadened scope for the use of hydrazones as neutral nucleophiles in the presence of H-bonding organocatalysts
Author/s | 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 |
Publication Date | 2006 |
Deposit Date | 2018-02-14 |
Published in |
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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 ... 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. |
Citation | 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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