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Current Organic Chemistry


ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

Synthetic Applications of Nitroalkanes Promoted by Solid Catalysis: Recent Results

Author(s): R. Ballini and A. Palmieri

Volume 10, Issue 17, 2006

Page: [2145 - 2169] Pages: 25

DOI: 10.2174/138527206778742632

Price: $65


Solid catalysis is crucial to chemical technology. Innumerable chemical reactions are facilitated by this catalytic system and, in this context, nitroalkanes have been demonstrated a great reactivity under solid catalysis, especially in the formation of new carbon-carbon single bond. In fact, aliphatic nitrocompounds are a valuable source of stabilized carbanions since the high electron-withdrawing power of the nitro group provides an outstanding enhancement of the hydrogen acidity at the α-position (cf. pKa MeNO2 = 10). Nitronate anions, that can be generated from nitroalkanes, using a wide range of bases, act as carbon nucleophiles with common electrophiles such as aldehydes (Nitroaldol-Henryreaction), and electron-poor alkenes (Michael reaction), leading to carbon-carbon bond formation. In the last few decades several solid catalyses have been efficiently proposed for the employment of the nitroalkanes in the latter reactions. Very often the use of nitroalkanes, combined with solid catalysis, offers the opportunity to perform the reactions more efficiently, with enhanced chemoselectivity, high purity, improved yields and without the use of any solvent.

Keywords: nitroalkanes, Mg-Al hydrotalcite, benzaldehydes Condensation, 1,3-Dinitropropanes, Michael Reaction, microwave irradiation

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