Reactions of 4-Methyl-2,6-diphenylphenol and 4-Nitro-2,6-diphenylphenol with Nitrogen Dioxide

1985 ◽  
Vol 38 (11) ◽  
pp. 1613 ◽  
Author(s):  
MP Hartshorn ◽  
RJ Martyn ◽  
WT Robinson ◽  
KH Sutton ◽  
J Vaughan ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Nitrogen Dioxide ◽  
Benzene Solution ◽  
Reaction Conditions ◽  
X Ray

Reaction of 4-methyl-2,6-diphenylphenol (11a) with nitrogen dioxide in benzene solution gives the polysubstituted cyclohex-2-enones (14), (15), (16), (17) and (18) via the 4-nitro dienone (13). The reversibility of the 4-nitro dienone (13)/4-hydroxy dienone (19) conversion under these reaction conditions is demonstrated. Reaction of 4-nitro-2,6-diphenylphenol (11b) with nitrogen dioxide in benzene solution gives the C2-epimeric 2,6-dihydroxy-4,5-dinitrocyclohex-3- enones (32) and (33) via the 6-nitro-6-phenyl dienone (12b). X-ray crystal structure analyses are reported for compounds (14), (15), (16), (17), (18) and (33).

The Formation of Monomeric and Dimeric Nitro Nitrates in the Reaction of Phenanthrene With Nitrogen Dioxide: X-Ray Crystal Structure of trans-10-Nitro-9,10-dihydrophenanthren-9-yl Nitrate

1990 ◽  
Vol 43 (1) ◽  
pp. 125 ◽  
Author(s):  
MC Judd ◽  
MP Hartshorn ◽  
RJ Martyn ◽  
WT Robinson ◽  
GJ Wright ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Liquid Chromatography ◽  
Nitrogen Dioxide ◽  
Benzene Solution ◽  
Gas Liquid Chromatography ◽  
X Ray ◽  
Product Yields

Reaction of phenanthrene (1) with nitrogen dioxide in benzene solution gives the dimeric nitro nitrate (3), trans and cis nitro nitrates (7) and (8), and 9-nitro- (4), 3-nitro- (5) and 1-nitro-phenanthrene (6). The X-ray crystal structure of the trans nitro nitrate (7) is reported. The effect of the phenanthrene (1) concentration on product yields is reported. Gas-liquid chromatography results for the nitro nitrates (3) and (7) point to difficulties in using this technique for product analyses in reactions of phenanthrene (1) with nitrogen dioxide.

The nitration of 2,4-dibromo-3,5,6-trimethylphenol and some reactions of polysubstituted phenols with nitrogen dioxide; X-ray crystal structure of 4-Acetyl-1-bromo-r-3,c-4-epoxy-2,t-5-dimethyl-3,5-dinitrocyclopentene

1983 ◽  
Vol 36 (8) ◽  
pp. 1589 ◽  
Author(s):  
MP Hartshorn ◽  
RJ Martyn ◽  
WT Robinson ◽  
KH Sutton ◽  
J Vaughan ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Acetic Acid ◽  
Nitric Acid ◽  
Nitrogen Dioxide ◽  
Reaction Conditions ◽  
X Ray ◽  
Fuming Nitric Acid

Nitrations of phenols (3a), (3b), (7) and (8) with nitrogen dioxide in cyclohexane give similar patterns of reaction to those with fuming nitric acid in acetic acid. Nitration of 2,4-dibromo-3,5,6-trimethyl- phenol (19) with nitrogen dioxide gives isomeric trinitrocyclohex-3-enones (24), while fuming nitric acid reactions yield either the trinitro ketone (24a) and the cis-dinitro ketone (25) or the C2-epimeric ketones (25) and (26) depending upon the reaction conditions. Some reactions of these products are described, and the X-ray crystal structure of the epoxycyclopentene derivative (30) is reported.

The Meisenheimer rearrangement in heterocyclic synthesis. II. Synthesis and X-ray crystal structure of a tetrahydro-1H-2,3-benzoxazocine and preparation of a hexahydro-2,3-benzoxazonine

1980 ◽  
Vol 33 (6) ◽  
pp. 1323 ◽  
Author(s):  
JB Bremner ◽  
EJ Browne ◽  
PE Davies ◽  
CLWAH Raston
Keyword(s):  
Molecular Structure ◽  
Crystal Structure ◽  
Acetic Acid ◽  
Crystal And Molecular Structure ◽  
Phosphorus Oxychloride ◽  
Crystallographic Analysis ◽  
Heterocyclic Synthesis ◽  
Reaction Conditions ◽  
X Ray ◽  
Heterocyclic Derivatives

The heterocyclic derivatives, 8,9-dimethoxy-3-methyl-1-phenyl-3,4,5,6- tetrahydro-1H-2,3-benzoxazocine(3a) and 9,10-dimethoxy-3-methyl-1- phenyl-1,3,4,5,6,7-hexahydro-2,3-benzoxazonine (3b),examples of two new ring systems, have been prepared by Meisenheimer rearrangement of the corresponding 2-benzazepine and 2-benzazocine N-oxide derivatives (2a) and (2b). The Bischler-Napieralski-type cyclization reaction was used in the preparation of the tertiary amine precursors of these N-oxides reaction conditions for the cyclization were critical and phosphorus oxychloride in refluxing butanenitrile was found to give the best yields of the seven- or eight-membered cyclic imine intermediates. Reductive cleavage of the benzoxazocine derivative (3a) with zinc in acetic acid followed by N-methylation gave the expected product, [2-{3- (dimethylamino)propyl}-4,5-di-methoxyphenyl]phenylmethanol (12). The crystal and molecular structure of (3a) has been determined by X-ray crystallographic analysis.

The Nitration of 4,6-Disubstituted 2-Phenylphenols. Some Structural Studies

1985 ◽  
Vol 38 (4) ◽  
pp. 575 ◽  
Author(s):  
MP Hartshorn ◽  
WT Robinson ◽  
J Vaughan ◽  
JM White
Keyword(s):  
Crystal Structure ◽  
Nitrogen Dioxide ◽  
Structural Studies ◽  
X Ray ◽  
Structure Determinations

Nitration of the bromophenols (4a) and (5a) give products of nitro-debromination . Reaction of 6-methyl-4-nitro-2-phenylphenol (5c) with nitrogen dioxide gives 2-hydroxy-2-phenylcyclohex-3-enones (8) and (9), and probably stereoisomers (10), (20), (21) and (22). The mode of ormation of these compounds is discussed. X-ray crystal structure determinations are reported for compounds (8) and (9).

The X-ray crystal structure of 4-t-Butyl-r-2-(4'-t-butyl-2',6'-dimethyl-phenoxy)-t-6-hydroxy-2,6-dimethyl-t-5-nitrocyclohex-3-enone

1984 ◽  
Vol 37 (6) ◽  
pp. 1369
Author(s):  
MP Hartshorn ◽  
KH Sutton ◽  
J Vaughan
Keyword(s):  
Crystal Structure ◽  
Nitrogen Dioxide ◽  
Structure Determination ◽  
Crystal Structure Determination ◽  
Reduced Pressure ◽  
X Ray

The X-ray crystal structure determination of 4-t-butyl-r-2-(4'-t-butyl-2',6'-dimethylphenoxy)-t-6- hydroxy-2,6-dimethyl-t-5-nitrocyclohex-3-enone (3) is reported. This compound is formed by reaction of 4-t-butyl-2,6-dimethylphenol(1) with nitrogen dioxide (1 mol) in benzene, followed by removal of the benzene under reduced pressure.

Kristall- und Molekülstruktur von 5.10-Dihydro-5.10-diniethylphenaziniiimtniodid und 5.10-Dihydro-5.10-diethylphenaziniumtriiodid / Molecular and Crystal Structure of 5,10-Dihydro-5.10-dimethylphenaziniumtriiodide and 5.10-Dihydro-5.10-diethylphenazinium triiodide

1978 ◽  
Vol 33 (8) ◽  
pp. 838-842 ◽  
Author(s):  
H. J. Keller ◽  
W. Moroni ◽  
D. Nöthe ◽  
M. Scherz ◽  
J. Weiss
Keyword(s):  
Crystal Structure ◽  
Radical Cations ◽  
Unit Cell ◽  
Lattice Parameters ◽  
Molecular And Crystal Structure ◽  
Reaction Conditions ◽  
Space Group ◽  
X Ray ◽  
R Value

Oxidation of 5,10-dihydro-5,10-dimethylphenazine and 5,10-dihydro-5,10-diethyl-phenazine under different reaction conditions leads to several iodine containing solids. The preparation and X-ray structure of two of them, 5,10-dihydro-5,10-dimethyl-phcnaziniumtriiodide (3) and 5,10-dihydro-5,10-diethylphenaziniumtriiodido (4) are reported here.Compound 3 crystallizes in space group P21/n with lattice parameters a = 8.552(6) Å, b= 16.953(2) Å, c- 12.157(9) Å and β= 103.46(2)° with four formula units in the unit cell. The structure was refined to an R-value of 0.046 using 2387 independent reflections. The lattice constains distinct, slightly distorted triiodide ions and bent 5,10-dihydro-5,10-dimethylphenazinium radical cations. Compound 4 crystallizes in the same space group P21/n with lattice parameters a = 8.531(6) Å, b = 8.332(21) Å, c = 13.320(15) Å and β= 94.44(19)° with two formula units in the unit cell. The structure was refined to an R-value of 0.076 using 1195 independent reflections. The lattice contains strictly linear symmetrical triiodide ions and planar centrosymmetrical 5,10-dihydro-5,10-diethyl- phenazinium radical cations.

scholarly journals Isonicotinamide-Based Compounds: From Cocrystal to Polymer

Molecules ◽  
2019 ◽  
Vol 24 (22) ◽  
pp. 4169
Author(s):  
Francisco Sánchez-Férez ◽  
Daniel Ejarque ◽  
Teresa Calvet ◽  
Mercè Font-Bardia ◽  
Josefina Pons
Keyword(s):  
Crystal Structure ◽  
Coordination Polymer ◽  
Coordination Mode ◽  
Lattice Energy ◽  
Hirshfeld Surface ◽  
Molar Ratio ◽  
Reaction Conditions ◽  
X Ray ◽  
The One ◽  
2D And 3D

The reaction between [Cu(μ-OAc)(μ-Pip)(MeOH)]2 (1) (OAc = acetate; Pip = 1,3-benzodioxole-5-carboxylate) and isonicotinamide (Isn) in MeOH as solvent yielded two mixture pairs of three compounds: {(HPip)2(Isn) (2), [Cu(Pip)2(Isn)2] (3)} and {(3), {[Cu3(Pip)2(OAc)2(μ-Isn)2(Isn)2(μ-OCH3)2(MeOH)2]·2MeOH}n (4)}. Modifying the reaction conditions (t, T, molar ratio), 2 and 3 have been successfully isolated, whereas 3 and 4 had to be mechanically separated. The recrystallization of 3 in pentanol yielded single crystals of compound [Cu(Pip)2(Isn)2]·C5H11OH (3a). The X-ray crystal structure of 2, 3a, and 4 has been elucidated showing a cocrystal, a monomer, and an unusual coordination polymer, respectively. The Pip ligand exhibited a chelate (3a) or a monodentate (4) coordination mode, but the Isonicotinamide (Isn) ligand is the one that promoted the arrangement of different structures and also mainly directs the formation of the 2D and 3D supramolecular assemblies. All the structures have been analyzed by Hirshfeld surface. In addition, the energy frameworks and lattice energy values of 2 and 3a have been calculated.

Photochemical Nitration by Tetranitromethane. XXXII. Adduct Formation in the Photochemical Reaction of Phenanthrene and Tetranitromethane

1996 ◽  
Vol 49 (4) ◽  
pp. 469
Author(s):  
CP Butts ◽  
L Eberson ◽  
KL Fulton ◽  
MP Hartshorn ◽  
WT Robinson
Keyword(s):  
Crystal Structure ◽  
Charge Transfer ◽  
Nitrogen Dioxide ◽  
Photochemical Reaction ◽  
Charge Transfer Complex ◽  
Major Product ◽  
Adduct Formation ◽  
X Ray ◽  
Structure Determinations ◽  
Ion Recombination

Photolysis of the phenanthrene/tetranitromethane charge-transfer complex yields the triad of phenanthrene radical cation, nitrogen dioxide, and trinitromethanide ion. Recombination of this triad in dichloromethane at 20° gives 9-nitrophenanthrene (1), trans-10-trinitromethyl-9,10-dihydrophenanthren-9-yl nitrate (2a), trans-9-nitro-10-trinitromethyl-9,10-dihydrophenanthrene (2b), and trans-10-trinitromethyl-9,10-dihydrophenanthren-9-ol (2c). Adduct formation is partially suppressed when trifluoroacetic acid (0.7 M) is added to the dichloromethane solvent at 20°, the major product identified being 9-nitrophenanthrene (1). At -20° in dichloromethane, or in acetonitrile at 20°, 10'-nitro-9,9',10,10'-tetrahydro-9,9'-biphenanthren-10-yl nitrate (3) is formed, apparently by reaction of nitrogen dioxide with phenanthrene. X-Ray crystal structure determinations are reported for adducts (2a,b).

1,3-Dipolar [3+3] Cycloaddition of 1,4-Benzodiazepinone-Based Nitrones with α-Halohydroxamates for Diastereoselective Synthesis of Novel d-Edge Heterocycle-Fused 1,4-Benzodiazepinones

Synlett ◽  
2021 ◽  
Author(s):  
Hong-Wu Zhao ◽  
Heng Zhang ◽  
Lu-Yu Cai ◽  
Zhe Tang ◽  
Xiao-Zu Fan ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Reaction Mechanism ◽  
Single Crystal ◽  
Structure Analysis ◽  
Crystal Structure Analysis ◽  
Diastereoselective Synthesis ◽  
Reaction Conditions ◽  
Relative Configuration ◽  
X Ray ◽  
Single Crystal Structure Analysis

Promoted by K2CO3 (2.0 equiv), the 1,3-dipolar [3+3] cycloaddition between 1, 4-benzodiazepinone-based nitrones and α-halohydroxamates processed smoothly under the mild reaction conditions and delivered structurally novel and complex cis or trans-configured d-edge-heterocycle-fused 1,4-benzodiazepinones in up to >99% isolated yield with >20:1 dr. The relative configuration of the title chemical entities was clearly identified with the use of X-ray single crystal structure analysis. The reaction mechanism was assumed to interpret the diastereoselective production of the obtained cis or trans-configured d-edge-heterocycle-fused 1, 4-benzodiazepinones.

Eine pentagonal pyramidale Koordination des Bismuts. Kristallstruktur von Methylbismutbis( diethyldithiocarbamat) / A Pentagonal Pyramidal Coordination of Bismut. Crystal Structure of Methylbismuthbis( diethyldithiocarbamate)

1979 ◽  
Vol 34 (7) ◽  
pp. 1037-1039 ◽  
Author(s):  
Christian Burschka ◽  
Markus Wieber
Keyword(s):  
Crystal Structure ◽  
Free Electron ◽  
Title Compound ◽  
Crystalline State ◽  
Electron Pair ◽  
Benzene Solution ◽  
X Ray Diffraction ◽  
X Ray ◽  
Free Electron Pair

Abstract Methylbismuth-bis(diethyldithiocarbamate), X-ray The crystal structure of the title compound, recrystallized from ethanol, was solved by means of X-ray diffraction methods and could be refined to an i?-value of 0.050 with 2126 reflections observed. In contrast to its behaviour in benzene solution, where the compound is monomeric, in the crystalline state dimeric units are formed by intermolecular Bi-S-interactions. The bismuth atoms are coordinated in form of a slightly distorted pentagonal pyramid with the free electron pair presumably directed opposite the apical C-atom.

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