Cracow University of Technology

Physical Organic Chemistry and Organocatalysis
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(E)-1-nitropent-1-ene
Substance index - selected nitrocompounds tested by our group /

CAS: 66022-60-4
MW: 115.132
Brutto formula: C5H9NO2
B.p. [oC]: 27-29/0.1-0.15mmHg [Ref.]
IR [cm-1]: 1642, 1519, 1350 [Ref.]
1H-NMR [ppm]: 7.28 (dt, 1H), 6.99 (d, 1H), 2.26, (q, 2H), 1.56 (sx, 2H), 0.99 (t, 3H) [Ref.]


Preparation [Ref.]:
One mole of sodium carbonate is added to a solution of two moles of nitropentyl acetate dissolved in 200 mL of anhydrous benzene and refluxed in a round-bottom flask for six hours. The flask is cooled and the product decanted from solids. The residue (sodium acetate) is extracted with benzene, dissolved in mater, and further extracted with small portions of benzene. The benzene solution is dried over K2CO3, the benzene distilled and the nitro alkene remaining is purified by distillation.


Applications:

Regio- and stereoselectivity of polar [2+3] cycloaddition reactions between (Z)-C-(3,4,5-trimethoxyphenyl)-N-methylnitrone and selected (E)-2-substituted nitroethenes
Jasiński R., Ziółkowska M. Demchuk O.M., Maziarka A.
Central European Journal of Chemistry, 12, 586-593 (2014)


Similar compounds: nitroethene, (E)-1-nitroprop-1-ene, (E)-1,1,1-trichloro-3-nitroprop-2-ene, (E)-2-phenyl-1-cyano-1-nitroethene




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