Journal Article10.1055/S-2004-829160
One-Pot Synthesis of 1,3-Dinitroalkanes under Heterogeneous Catalysis
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TL;DR: In this paper, aldehydes with an excess of nitromethane in the presence of basic alumina as solid catalyst allows the one-pot preparation of 1,3-dinitroalkanes.
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Abstract: Reaction of aldehydes with an excess of nitromethane in the presence of basic alumina as solid catalyst allows the one pot preparation of 1,3-dinitroalkanes. The synthesis proceeds through the nitroaldol reaction of nitromethane, which acts both as nucleophile and as solvent, to the aldehydes with the formation of β-nitroalkanols as intermediates that convert to nitroalkenes. Further nucleophilic behavior of the nitromethane produces the in situ conjugate addition of its carbanion to the formed nitroalkenes giving the one-pot synthesis of the title compounds. The catalyst shows general applicability with aliphatic, aromatic and heteroaromatic aldehydes.
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Citations
Conjugate Additions of Nitroalkanes to Electron-Poor Alkenes: Recent Results
TL;DR: This review is focused on the utilization of nitroalkanes as nucleophiles in conjugate additions with electron-poor alkenes and covers the new procedures and related applications appearing in the literature after 1990.
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Synthesis of C1-symmetric chiral secondary diamines and their applications in the asymmetric copper(II)-catalyzed Henry (nitroaldol) reactions.
TL;DR: The low catalyst loading, excellent yields and enantioselectivities, inexpensive copper salt, and mild reaction conditions make the catalytic system to be practically useful.
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Highly Enantioselective Direct Michael Addition of Nitroalkanes to Nitroolefins Catalyzed by La(OTf)3/N,N′‐Dioxide Complexes
TL;DR: The direct asymmetric Michael addition of unmodifiedNitroalkanes to nitroalkenes is described by using lanthanum(III) triflate in combination with an N,N’-dioxide ligand.
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