Heterogeneous catalysts in the preparation of 2-aryl-1,3-dinitropropanes from beta-nitrostyrenes or benzaldehydes
Angélica Fierro, Marcos Caroli Rezende, Silvia Sepúlveda-Boza, Miguel Reyes-Parada and Bruce K. Cassels
J. Chem. Research (S), 2001, 294–296
Abstract
The use of heterogeneous basic catalysts (KF, NaHCO3) in the preparation of 2-Aryl-1,3-dinitropropanes from beta-nitrostyrenes or benzaldehydes is described, with one example followed kinetically by HPLC analysis of aliquots of the reaction.
(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_imgs/pdf.gif)
.pdf made available by Kinetic in record time - thanks ;D
General preparation of 1-aryl-2-nitroethenes:
A solution of the corresponding benzaldehyde (10 mmol), nitromethane (20 mmol) and n-butylamine (1 mL) in glacial acetic acid (10 mL) was refluxed for 1 hour. The 1-aryl-2-nitroethene which separated upon cooling, was filtered and recrystallized in methanol. In this way the following nitroethenes were prepared:
1-(3,4-methylenedioxyphenyl)-2-nitroethene 87%
1-(3,4,5-trimethoxyphenyl)-2-nitroethene 84%
1-(2,5-dimethoxyphenyl)-2-nitroethene 88%
...some other nitrostyrenes are reported in the original article.
--psyloxy--
It's from Rhodium's... (there should be a markup button for these words, too!)
"Ethylenediammonium diacetate - a novel nitrostyrene synthesis catalyst"
https://www.thevespiary.org/rhodium/Rhodium/chemistry/edda.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/edda.html)
Also very interesting due to exceptionally high yields with certain substrates: The use of plain ethylenediamine w/o any GAA...
Post 508451 (missing)
(azole: "ethylenediamine as a catalyst", Methods Discourse)
...but 2h rxn time seems pretty unbeatable! Except with methanolic, anhydrous methylamine maybe... :P
And I really wonder if there would be any advantage in making the acetic salt of butylamine and use that as catalyst - just like is done with ethylenediamine...
Greetz A