104489-00-1Relevant articles and documents
A new conversion of primary nitro compounds into nitriles
El Kaim, Laurent,Gacon, Ariane
, p. 3391 - 3394 (1997)
The reaction of primary nitro compounds with isocyanides and isocyanates in the presence of a base leads to a new preparation of nitriles. The reaction probably proceeds through the in situ formation of a nitrile oxide followed by a fast oxygen transfer with the isocyanide. Combined with the Knovenagel addition of nitromethane to cyclic ketone, this reaction brings a highly effective regioselective formation of cyclic α-β unsaturated nitriles.
A MILD PROCEDURE FOR THE REDUCTION OF ALIPHATIC NITRO COMPOUNDS TO OXIMES
Barton, Derek H. R.,Fernandez, Isabel,Richard, Caroline S.,Zard, Samir Z.
, p. 551 - 558 (2007/10/02)
Aliphatic nitro compounds react with carbon disulphide in the presence of triethylamine to give the corresponding oximes in moderate to good yields.
Facile Synthesis of Allylic Nitro Compounds by N,N-dimethylethylenediamine-Catalyzed Condensation of Aliphatic and Alicyclic Ketones with Primary Nitroalkanes
Tamura, Rui,Sato, Masahiro,Oda, Daihei
, p. 4368 - 4375 (2007/10/02)
Aliphatic as well as alicyclic ketones condense with primary nitroalkanes in the presence of N,N-dimethylethylenediamine (1) to give allylic nitro compounds selectively in good to excellent yields without forming α-nitro olefins.Condensation of 2-alkanones and 2-methylcyclopentanone with nitromethane produces the products of thermodynamic control, while the product of kinetic control is obtained from 2-methylcyclohexanone.Propiophenone, an aromatic ketone, reacted with nitromethane in a way analogous to aliphatic ketones to give the corresponding allylic nitro product.A reaction mechanism to account for the exclusive formation of allylic nitro compounds is proposed.Some allylic nitro compounds thus obtained are converted into α,β-unsaturated aldehydes and ketones by treatment with sodium methoxide and then TiCl3 in buffered solution.
