Synthesis 2004(12): 1938-1940  
DOI: 10.1055/s-2004-829160
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

One-Pot Synthesis of 1,3-Dinitroalkanes under Heterogeneous Catalysis

Roberto Ballini*, Giovanna Bosica, Dennis Fiorini, Alessandro Palmieri
Dipartimento di Scienze Chimiche, Università di Camerino, Via S. Agostino 1, 62032 Camerino (MC), Italy
Fax: +39(0737)402297; e-Mail: roberto.ballini@unicam.it;
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Publikationsverlauf

Received 19 April 2004
Publikationsdatum:
21. Juli 2004 (online)

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.