2- Nitro-l-propene

Dehydration of P-nitro alcohols provides an important method for the preparation of nitroalkenes. Because lower nitroalkenes such as nitroethylene, 1-nitro-1-propene, and 2-nitro-l-propene tend to polymerize, they must be prepared carefully and used immediately after preparation. Dehydration with phthalic anhydride is the most reliable method for such lower nitroalkenes.42,43 Such lower nitroalkenes have been used as important reagents for Michael acceptors or dienophiles in the Diels-Alder reaction, which will be... 

Nitro-l-propene Preparation is accomplished by dehydration of l-nitro-2-propanol with methanesulfonyl chloride and triethylamine (30% yield),47 acetic anhydride-AcONa (85% yield),46 or phthalic anhydride (55%)45 bp 58 °C/35 mmHg (Eq. 3.25). 

Nitroethylene, 1-nitro-l-propene and 2-nitro-l-propene, see Encyclopedia of Reagents for Organic Synthesis, ed. by L. Paquette, Wiley, New York, 1996. 

Frankel synthesized 2-nitro-3-acetoxy-l-propene (139) by heating l,3-diacetoxy-2-nitropropane (138) with sodium acetate under reduced pressure. The reaction of 2-nitro-3-acetoxy-l-propene with 1,1-dinitroethane yields 2,2,4,6,6-pentanitroheptane. The same reaction with nitroform provides 1,1,1,3,5,5,5-heptanitropentane (142), a powerful explosive (VOD 9230 m/s) with an excellent oxygen balance. The synthesis of 1,1,1,3,5,5,5-heptanitropentane from2-nitro-l,3-propanediol and 2-nitro-l-propen-3-ol has also been reported and involves a similar mechanism. 

Polymerization of 2-nitro l propene is less vigorous (the heal of polymerization is 13.0 kcal./inol at 20 ( ). The polymer is a viscous liquid or a brittle solid. 

The chemical stability of the polymers of both nitrocthyleno and 2-nitro l-propene is low. Tliis is partly due. to the traces of catalysis present in the polymers which can act as decomposition catalysis. Poly(nitrocthylcnc) turns... 

A mixture consisting of 250 g. (1.53 mols) of l-phenyl-2-nitro-l propene, 85 cc. (1.48 equivalents of acetic acid, 600 cc. of methanol and... 

Nitropropane 3-Nitropropanoicacid 2-Nitro-l-propanol 1-Nitro-l-propene 2-Nitro-l-propene... 

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