A new synthesis of conjugated nitro cyclo olefins, unusually versatile synthetic intermediates

A DFT computational study on the [3+2] cycloaddition between parent thionitrone and nitroethene

“…[13][14][15][16] Furthermore, nitro-group is an exceedingly attractive starting point for further transformation into many important organic groups and moieties. [17][18][19][20] Nitroisothiazolidines can be prepared via [3+2] cycloaddition reaction involving thionitrones and conjugated nitroalkenes as addents. Unfortunately, there has been no relevant research so far dedicated the cycloaddition reaction of conjugated nitroalkenes with thionitrones.…”

DFT study of the decomposition reactions of nitroethyl benzoates catalyzed by the 1,3-dimethylimidazolium cation

“…Recently published reports 26,[44][45][46][47][48] , indicate that a similar approach was used successfully for the exploration of a reaction involving several different nitrocompounds. These calculations proved that the first step of the decomposition of nitroethyl benzoate (1a) is the establishment of a pre-reaction complex ( [1][DMIM]) between the ester molecule and the 1,3-dimethylimidazolium cation. Consequently, the creation of a pre-reaction complex entails the drop of reaction enthalpy by 3.54 kcal·mol -1 ( Fig.…”

“…Conjugated nitroalkenes (CNA) have been recognized as versatile synthetic intermediates in various organic syntheses because of their easy conversion to a variety of diverse functionalities. [1][2][3][4][5] They react as dienophiles, heterodienes, 1,3-dipoles and, above all, as Michael acceptors. [6][7][8] Conjugated nitroalkenes are also distinguished by their biological properties.…”

“…13 Several methods are available for the preparation of nitroalkenes. 1,[17][18][19][20] However, a great demand still exists for a method to prepare nitroolefins in a convenient and effective way. The present work is a continuation of our comprehensive study about the synthesis and fundamental properties of CNA.…”

Synthesis of Polysubstituted Pyrrolizidines from Proline Derivatives and Conjugated Nitroolefins

“…Nitroolefns. (E)-P-Nitrostyrene (= (E)-(2-nitroethenyl)benzene; 7c) was purchased from Aldrirh Chemicals; (E)-I-nitropropene (7a) [19], 2-nitropropene (7b) [I91 (E)-2-nitro-l-phenylpropene (= (E)-(2-nitroprop-leny1)benzene; 7d) [20], ar-nitrostilbene (= (E)-I ,1'-(1 -nitroethen-1,2-diyl)bis[benzene]; 7e) [21], I-nitrocyclopentene (70 1221, and I-nitrocyclohexene (7g) [22] were prepared by literature procedures.…”