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Egypt February 22-25 2007  Green
Chemistry   One-Pot Synthesis of Fine Chemicals
Promoted by Nitroalkanes  Roberto
Ballini  Dipartimento di Scienze
Chimiche Università di Camerino Camerino (MC)
Italy Fax [phone] Tel.
39-0737-402270 e-mail roberto.ballini_at_unicam.it
 
                   
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Multistep Synthetic Process
Large amounts of waste products!!!!
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Advantages of the One-Pot Process

• Reduction of amount of solvents
• Reduction of amount of catalysts
• Reduction of purification steps
• Reduction of the work-up steps
• The one-pot process can drive the equilibria
• to the desired direction!

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How can we plan a one-pot process?
The One-Pot Process can be favoured by

• Appropriate choice of the catalysts

2) Appropriate choice of the reaction conditions
3) Appropriate addition sequence of the starting
materials
4) Appropriate choice of the starting materials
(with an high Chemical versatility).
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Chemical Versatility of Nitroalkanes
-Easily conversion into other functionalities
-Formation of C,C single bond
-Cleavage of C,C bond
-Formation of C,C double bond
-The Nitro Group can be substituted, after its
use, by an hydrogen
-The Nitro Group is a good leaving group.
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Formation of C,C double bonds through the Michael
Reaction
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Ring Cleavage of Cyclic Ketones
w-funtionalized nitro derivatives
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D. Seebach et al. Chimia 1979, 33, 1-18
Are Nitroaliphatic Compounds Ideal
Intermediates in Organic Synthesis?
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Synthesis of Fine Chemical in a One-Pot or in a
Double . One-Pot way, from Nitroalkanes, Decrea
sing the Amount of Waste Products!!!
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Nitroaldol Condensation
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Michael Reaction Formation of C,C Single Bond
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EWG COR, COOR, CHO
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Key Building blocks for the synthesis of -Nitro
Sugar Derivatives -Antibiotics -Pheromones.
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(2 moles)
One-pot
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Michael Reaction Formation of C,C Double Bond
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One-pot Synthesis of Benzoate and Acetophenone
Derivatives
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Tandem Ring Closure-Michael addition-Elimination
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High-Energy Density Materials, often, are organic
compounds that have nitro groups in them!
Dinitrocyclopropanes
Nitrocycloprone(a)nes
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Ballini, R. Fiorini, D. Palmieri, A. Synlett
2003, 1704
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Are Nitroaliphatic Compounds Ideal
Intermediates in Organic Synthesis?
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