The Stereochemistry of SRN1 Reactions in Nitroacenaphthenes

1987 ◽  
Vol 40 (3) ◽  
pp. 523 ◽  
Author(s):  
FI McLure ◽  
RK Norris
Keyword(s):  
Nitro Group ◽  
Reaction Site ◽  
Aromatic Rings ◽  
Ethyl Group ◽  
Benzylic Carbon ◽  
Alkyl Groups ◽  
The Face

The reaction of the 2-chloro-1,l-dialkyl-6-nitroacenaphthenes (1)-(3) with azide and p- toluenethiolate ions takes place by the SRN1 mechanism, to give the substitution products (27)-(32), despite the fact that the nitro group and the chlorine-bearing benzylic carbon are attached to different aromatic rings. The reaction of the stereoisomers (2) and (3) of 2-chloro-1-ethyl-1-methyl-6-nitroacenaphthene takes place through an effectively planar benzylic radical (35), which is preferentially attacked from the face remote from the a-ethyl group. The presence of geminal alkyl groups α to the reaction site in the rigid acenaphthene system restricts the scope of the substitution processes to sterically unhindered nucleophiles, and the reaction fails with reagents such as sodium p- toluenesulfinate (23) and the salts, (24) and (25), derived from 2-ethylmalononitrile and 2-nitropropane.

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].

scholarly journals Methyl 2,4-dihydroxy-5-(4-nitrobenzamido)benzoate

2013 ◽  
Vol 69 (2) ◽  
pp. o207-o207
Author(s):  
Syeda Sohaila Naz ◽  
Nazar Ul Islam ◽  
M. Nawaz Tahir ◽  
Muhammad Raza Shah
Keyword(s):  
Hydrogen Bonds ◽  
Nitro Group ◽  
Dihedral Angle ◽  
Title Compound ◽  
Three Dimensional ◽  
Aromatic Rings ◽  
Compound C ◽  
Dimensional Network

In the title compound, C15H12N2O7, the dihedral angle between the aromatic rings is 4.58 (13)° and the nitro group is rotated from its attached ring by 18.07 (17)°. Intramolecular N—H...O and O—H...O hydrogen bonds generateS(5) andS(6) rings, respectively. In the crystal, molecules are linked by O—H...O hydrogen bonds, generating [001]C(7) chains. The chains are linked by C—H...O interactions, forming a three-dimensional network, which incorporatesR22(7) andR22(10) loops.

Syntheses of cytotoxic novel arctigenin derivatives bearing halogen and alkyl groups on aromatic rings

2017 ◽  
Vol 27 (17) ◽  
pp. 4199-4203 ◽  
Author(s):  
Satoshi Yamauchi ◽  
Tuti Wukirsari ◽  
Yoshiaki Ochi ◽  
Hisashi Nishiwaki ◽  
Kosuke Nishi ◽  
...  
Keyword(s):  
Aromatic Rings ◽  
Alkyl Groups

ChemInform Abstract: Hydrosilanes Are not Always a Reducing Reagent: A Ruthenium-Catalyzed Introduction of Primary Alkyl Groups to Electron-Rich Aromatic Rings Using Esters as a Source of the Alkyl Groups.

ChemInform ◽  
2012 ◽  
Vol 43 (7) ◽  
pp. no-no
Author(s):  
Hideo Nagashima ◽  
Yuichi Kubo ◽  
Mitsunobu Kawamura ◽  
Takashi Nishikata ◽  
Yukihiro Motoyama
Keyword(s):  
Aromatic Rings ◽  
Alkyl Groups

Alkyl transfer from C–C cleavage: replacing the nitro group of nitro-olefins

2014 ◽  
Vol 50 (47) ◽  
pp. 6246-6248 ◽  
Author(s):  
Guangxun Li ◽  
Lei Wu ◽  
Gang Lv ◽  
Hongxin Liu ◽  
Qingquan Fu ◽  
...  
Keyword(s):  
Nitro Group ◽  
Alkyl Transfer ◽  
Alkyl Groups

Hydrogenation is only the beginning: alkyl groups are mildly transferred from alkyl substituted Hantzsch esters to replace the nitro groups of nitro olefins to providetrans-olefins in moderate to excellent yields.

scholarly journals Triethylammonium 1,3-dimethyl-5-(2,4,6-trinitrophenyl)barbiturate

2012 ◽  
Vol 68 (8) ◽  
pp. o2395-o2395 ◽  
Author(s):  
Kulandaiya Rajamani ◽  
Doraisamyraja Kalaivani
Keyword(s):  
Hydrogen Bond ◽  
Nitro Group ◽  
Dihedral Angle ◽  
Aromatic Rings ◽  
Ring Plane ◽  
Ring Junction ◽  
Supramolecular Chains ◽  
Molecular Salt

In the title molecular salt [systematic name: triethylammonium 1,3-dimethyl-2,6-dioxo-5-(2,4,6-trinitrophenyl)-1,2,3,6-tetrahydropyrimidin-4-olate], C6H16N+·C12H8N5O9−, the dihedral angle between the aromatic rings in the anion is 46.88 (8)°. The nitro groupparato the ring junction is almost coplanar with its attached ring [dihedral angle = 0.76 (3)°], but the twoortho-nitro groups are substantially twisted from the ring plane, by 47.91 (2) and 42.90 (1)°. In the crystal, the cation and anion are linked by an N—H...O=C hydrogen bond; these dimeric associations are further connected by weak C—H...O bonds to form linear supramolecular chains extending in the [001] direction.

Oxidation of alkyl groups accompanying the Zinin reduction of nitroarenes

1977 ◽  
Vol 30 (4) ◽  
pp. 927 ◽  
Author(s):  
DA Burgess ◽  
ID Rae
Keyword(s):  
Nitro Group ◽  
Methyl Group ◽  
Alkyl Groups

p-Aminobenzaldehydes have been prepared from several nitroxylenes and trimethylnitrobenzenes by reaction with aqueous alcoholic sodium polysulphide. The oxidation of the methyl group accompanying the Zinin reduction proceeds most readily when the nitro group is unhindered.

Powder diffraction analysis of an interstratified marcasite/pyrite structure

1995 ◽  
Vol 10 (3) ◽  
pp. 198-203 ◽  
Author(s):  
Neil E. Johnson ◽  
Sidney S. Pollack ◽  
Elizabeth A. Frommell ◽  
Patricia A. Eldredge
Keyword(s):  
Catalytic Activity ◽  
Stacking Faults ◽  
Catalyst Precursor ◽  
X Ray Diffraction ◽  
Aromatic Rings ◽  
X Ray ◽  
Naturally Occurring ◽  
Benzylic Carbon ◽  
Diffraction Peaks ◽  
Diffraction Patterns

A synthetic catalyst precursor formed by sulfiding ferrihydrite (Fe3+O(OH)) in the presence of a hydrogen donor produces X-ray diffraction patterns resembling a mixture of both naturally occurring FeS2 polymorphs marcasite and pyrite. The diffraction peaks display a differential broadening, however, wherein only those peaks coincident to both marcasite and pyrite are strong and sharp, a feature that cannot be accounted for by a simple physical mixture. The broadening is analogous to that found in hexagonal cobalt, where occasional stacking faults produce interstratification of the hexagonal and cubic close-packed forms, resulting in strongly coherent diffraction only along the stacking direction. The crystal structures of marcasite and pyrite are virtually identical if viewed perpendicular to the (101) and (001) planes, respectively. Calculation of diffraction patterns based upon models of interstratifying marcasite and pyrite layers along these planes demonstrates that a sequence with marcasite-to-pyrite and pyrite-to-marcasite stacking fault probabilities of 0.22 provides a good fit to the experimental pattern. This interstratified material is a precursor to a species that shows catalytic activity for cleaving C-C bonds between aromatic rings and benzylic carbon atoms at low (<350 °C) temperatures.

scholarly journals 3-Chloro-1-ethyl-6-nitro-1H-indazole

IUCrData ◽  
2017 ◽  
Vol 2 (7) ◽  
Author(s):  
Mohamed Mokhtar Mohamed Abdelahi ◽  
Nada Kheira Sebbar ◽  
Jerry P. Jasinski ◽  
Manpreet Kaur ◽  
El Mokhtar Essassi ◽  
...  
Keyword(s):  
Nitro Group ◽  
Dihedral Angle ◽  
Title Compound ◽  
Ring System ◽  
Stacking Interactions ◽  
Ethyl Group ◽  
Compound C ◽  
Π Stacking

In the title compound, C9H8ClN3O2, the terminal C atom of the ethyl group deviates from the indazole ring (r.m.s. deviation = 0.008 Å) by 1.588 (3) Å. The dihedral angle between the ring system and the attached nitro group is 2.8 (3)°. In the crystal, weak C—H...O interactions link the molecules into zigzag chains propagating along [001]. In addition, weak π–π stacking interactions [centroid–centroid separations = 3.6809 (10) and 3.7393 (11) Å] help to consolidate the packing.

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