Intramolecular condensation of nitro group with olefinic double bond

1968 ◽  
Vol 17 (2) ◽  
pp. 357-363 ◽  
Author(s):  
L. A. Simonyan ◽  
N. P. Gambaryan ◽  
P. V. Petrovskii ◽  
I. L. Knunyants
Keyword(s):  
Double Bond ◽  
Nitro Group ◽  
Intramolecular Condensation ◽  
Olefinic Double Bond

scholarly journals Crystal structure of (3E)-3-(2,4-dinitrophenoxymethyl)-4-phenylbut-3-en-2-one

2014 ◽  
Vol 70 (9) ◽  
pp. o1051-o1052 ◽  
Author(s):  
Ignez Caracelli ◽  
Stella H. Maganhi ◽  
Paulo J. S. Moran ◽  
Bruno R. S. de Paula ◽  
Felix N. Delling ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Double Bond ◽  
Nitro Group ◽  
Benzene Ring ◽  
Torsion Angle ◽  
Title Compound ◽  
Phenyl Ring ◽  
Aromatic Rings ◽  
Compound C ◽  
The One

In the title compound, C17H14N2O6, the conformation about the C=C double bond [1.345 (2) Å] isE, with the ketone moiety almost coplanar [C—C—C—C torsion angle = 9.5 (2)°] along with the phenyl ring [C—C—C—C = 5.9 (2)°]. The aromatic rings are almost perpendicular to each other [dihedral angle = 86.66 (7)°]. The 4-nitro moiety is approximately coplanar with the benzene ring to which it is attached [O—N—C—C = 4.2 (2)°], whereas the one in theorthoposition is twisted [O—N—C—C = 138.28 (13)°]. The molecules associateviaC—H...O interactions, involving both O atoms from the 2-nitro group, to form a helical supramolecular chain along [010]. Nitro–nitro N...O interactions [2.8461 (19) Å] connect the chains into layers that stack along [001].

ChemInform Abstract: Electroreduction of the Activated Olefinic Double Bond in Some 2-Aryl-1(2-acetylamino-1,3,4-thiadiazol-5-yl)-propionitrile Derivatives

ChemInform ◽  
1987 ◽  
Vol 18 (23) ◽  
Author(s):  
M. ABDEL AZZEM ◽  
M. M. M. RAMIZ ◽  
E. A. GHALI ◽  
H. M. FAHMY ◽  
M. R. H. ELMOGHAYAR
Keyword(s):  
Double Bond ◽  
Olefinic Double Bond

scholarly journals Cathodic hydrodimerization of nitroolefins

2015 ◽  
Vol 11 ◽  
pp. 1163-1174 ◽  
Author(s):  
Michael Weßling ◽  
Hans J Schäfer
Keyword(s):  
Double Bond ◽  
Nitro Group ◽  
Bond Formation ◽  
Cathodic Reduction ◽  
High Yield ◽  
Easy Access ◽  
Electrolysis Cell ◽  
Aldehydes And Ketones ◽  
Nef Reaction

Nitroalkenes are easily accessible in high variety by condensation of aldehydes with aliphatic nitroalkanes. They belong to the group of activated alkenes that can be hydrodimerized by cathodic reduction. There are many olefins with different electron withdrawing groups used for cathodic hydrodimerization, but not much is known about the behaviour of the nitro group. Synthetic applications of this group could profit from the easy access to nitroolefins in large variety, the C–C bond formation with the introduction of two nitro groups in a 1,4-distance and the conversions of the nitro group by reduction to oximes and amines, the conversion into aldehydes and ketones via the Nef reaction and base catalyzed condensations at the acidic CH bond. Eight 1-aryl-2-nitro-1-propenes have been electrolyzed in an undivided electrolysis cell to afford 2,5-dinitro-3,4-diaryl hexanes in high yield. The 4-methoxy-, 4-trifluoromethyl-, 2-chloro- and 2,6-difluorophenyl group and furthermore the 2-furyl and 2-pyrrolyl group have been applied. The reaction is chemoselective as only the double bond but not the nitro group undergoes reaction, is regioselective as a ß,ß-coupling with regard to the nitro group and forms preferentially two out of six possible diastereomers as major products.

Oxydation du cyclohexène par le nitrate cérique d'ammonium

1974 ◽  
Vol 52 (18) ◽  
pp. 3201-3205 ◽  
Author(s):  
Claude Briguet ◽  
Christian Freppel ◽  
Jean-Claude Richer ◽  
Miklos Zador
Keyword(s):  
Double Bond ◽  
Ammonium Nitrate ◽  
Ceric Ammonium Nitrate ◽  
Olefinic Double Bond

The oxidation of cyclohexene by ceric ammonium nitrate has been studied. In anhydrous DMSO the reaction leads to cyclohexene-3-nitrate, while in acetonitrile N-(cyclohexene-2-yl) acetamide is formed. Hydroxylated products are formed in the presence of water. The results obtained are explained in terms of the formation of an intermediate arising from the addition of the radical NO3• to the olefinic double bond. [Journal translation]

Electrochemical Heterodifunctionalization of α-CF3 Alkenes to Access α-Trifluoromethyl-β-sulfonyl Tertiary Alcohols

2021 ◽  
Author(s):  
Zhi-Peng Ye ◽  
Jie Gao ◽  
Xin-Yu Duan ◽  
Jianping Guan ◽  
Fang Liu ◽  
...  
Keyword(s):  
Double Bond ◽  
Hydroxyl Group ◽  
Tertiary Alcohols ◽  
Olefinic Double Bond

An unprecedented electrochemical heterodifunctionalization of α-CF3 alkenes with benzenesulfonyl hydrazides was accomplished in this work, wherein a β-sulfonyl and a α-hydroxyl group were simultaneously incorporated across the olefinic double bond...

Reductive Condensation of a Nitro Group with Carboxylic Acids Promoted by Phosphorus(III) Compounds: A Short Route to 5H-Dibenzo[b,e][1,4]diazepin-11(10H)-ones

Synthesis ◽  
2020 ◽  
Author(s):  
Zbigniew Wróbel ◽  
Michał Tryniszewski ◽  
Robert Bujok ◽  
Roman Gańczarczyk
Keyword(s):  
Nitro Group ◽  
Carboxylic Acids ◽  
Carboxyl Group ◽  
Short Route ◽  
Step Method ◽  
One Pot ◽  
Aryl Group ◽  
Intramolecular Condensation ◽  
Reductive Condensation

Tributyl- or triphenylphosphine promotes a one-pot, three-step method for the synthesis of differently substituted dibenzodiazepinones from N-aryl-2-nitroanilines. Pyridine analogues and the corresponding thiazepinones can also be formed using this method. The process involves deoxygenation of the nitro group, then formation of an iminophosphorane intermediate and its intramolecular condensation with a carboxyl group placed in the N-aryl group. The role of the carboxyl group in the formation of the iminophosphorane and the mode of cyclization are discussed.

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