Condensed Cyclobutane Aromatic Compounds. XIV. Naphtho[b]cyclobutene: Reactions of the Aromatic Nucleus

1961 ◽  
Vol 26 (7) ◽  
pp. 2212-2215 ◽  
Author(s):  
M. P. CAVA ◽  
R. L. SHIRLEY
2006 ◽  
Vol 61 (4) ◽  
pp. 448-463 ◽  
Author(s):  
Willi Kantlehner ◽  
Ralf Kreß ◽  
Franziska Zschach ◽  
Jens Vetter ◽  
Georg Ziegler ◽  
...  

The reagent system formed from tris(dichloromethyl)amine (5) and aluminium chloride allows the formylation of aromatic compounds. The scope of the method is comparable with that of the Olah formylation and the Groß-Rieche procedure, since benzene and even chlorobenzene can be formylated. One formyl group is transferred from 5 to the aromatic nucleus. In order to find optimal reaction conditions, the molar amounts of aromatic compounds, 5 and aluminum chloride were varied as well as reaction temperatures and solvents. The activation of 5 with other Lewis acids is also described


1983 ◽  
Vol 61 (3) ◽  
pp. 533-540 ◽  
Author(s):  
Stanislas Czernecki ◽  
Veronique Dechavanne

The arylation of peracetylated glycals catalyzed by palladium salts provides a new synthesis of C-glycosides. The title reaction is applied to several aromatic compounds, including fluoro and nitro derivatives. The regioselectivity of the reaction with respect to the aromatic nucleus is explained by the formation of an arylpalladium directly from the aromatic compound and the salt. A two-step mechanism, involving syn-addition of the arylpalladium to the glycal double bond, followed by a syn-elimination is proposed and discussed.


The structure of the halogenobenzenes is described in terms of an inductive effect acting on the meta -positions and polarization between neighbouring atoms, in addition to the well-recognized mesomeric and inductive effects at the ortho - and para -positions. Data on the side-chain reactions of aromatic compounds are correlated with those on nitration (with recognition of the effect of transition-state resonance in the latter case) to provide estimates of the charge distribution in the aromatic nucleus. The dipole moments of the halogenobenzenes are calculated.


The dipole moments of organic substances represent the resultants of a number of distinct moments within the molecule form which they must, as was pointed out by Sir J. J. Thomson, be obtainable by vector summation. This view was extended and further examined by Eucken and Meyer in 1929. It has been generally accepted and confirmed for a large variety of substances. The figures for para -disubstituted benzene derivatives of the type X. C 6 H 4 . Y are of particular importance for two reasons. First, it was anticipated by Ingold on the ground of the electronic theory of aromatic reactivity, that some deviation from the additive law might occur in this class of compound when Y was a group such as —NR 2 as a result of electronic displacements in the aromatic nucleus. When the necessary data became available by the measurements of Højendahl, a gross discrepancy of this kind appeared probable for p -nitraniline and p -nitroanisole, and this was specifically emphasized at that time. Secondly, a number of workers have recently made use of dipole moment data for aromatic ethers and sulphides of this same general type in order to compute the angle between the valencies of the characteristic atom (oxygen and sulphur) of the group Y.


1964 ◽  
Vol 42 (9) ◽  
pp. 2065-2072 ◽  
Author(s):  
Helmut Huber ◽  
George F Wright

Diphenylmercury has been used as a model to show that the electron and atom parts of the distortion polarization cannot reliably be evaluated by optical methods. The measured electron polarization extrapolated to infinite wavelength is larger than the combined electron and atom polarization measured at radio frequency. The difference has been defined as the "phenyl effect" and has been attributed to the mobility at radio frequencies of electrons in the resonance-hybridized orbitals of the aromatic nucleus. It has been suggested that the effect is general for aromatic compounds.


2016 ◽  
Vol 94 (suppl_5) ◽  
pp. 818-818
Author(s):  
K. R. Wall ◽  
C. R. Kerth ◽  
T. R. Whitney ◽  
S. B. Smith ◽  
J. L. Glasscock ◽  
...  

2017 ◽  
Author(s):  
Xueming Dong

Catalytic deoxygenation of coal enhances the stability and combustion performance of coal-derived liquids. However, determination of the selectivity of removal of oxygen atoms incorporated in or residing outside of aromatic rings is challenging. This limits the ability to evaluate the success of catalytic deoxygenation processes. A mass spectrometric method, in-source collision-activated dissociation (ISCAD), combined with high resolution product ion detection, is demonstrated to allow the determination of whether the oxygen atoms in aromatic compounds reside outside of aromatic rings or are part of the aromatic system, because alkyl chains can be removed from aromatic cores via ISCAD. Application of this method for the analysis of a subbituminous coal treated using a supported catalyst revealed that the catalytic treatment reduced the number of oxygen-containing heteroaromatic rings but not the number of oxygen atoms residing outside the aromatic rings.<br>


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