Mechanism of alkenylation of aromatic substrates with 5-nitro-2-furylvinyl bromide

1986 ◽  
Vol 51 (9) ◽  
pp. 2013-2018
Author(s):  
Ján Hrabovský ◽  
Jaroslav Kováč ◽  
František Považanec
Keyword(s):  
Electrophilic Addition ◽  
Point Of View ◽  
Electrophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
H Nmr ◽  
Aromatic Substrates ◽  
Nmr Study ◽  
Elimination Pathway

Mechanism has been studied of electrophilic aromatic substitution with (Z)- and (E)-5-nitro-2-furylvinyl bromide in the presence of aluminium(III) chloride. From chemical findings and 1H NMR study it follows that the mechanism can be interpreted as an electrophilic addition-elimination pathway (AdE-E) from the point of view of the vinyl substitution.

Synthesis of Aromatic and Aliphatic Di-, Tri-, and Tetrasulfonic Acids

Synlett ◽  
2020 ◽  
Vol 31 (10) ◽  
pp. 945-952
Author(s):  
Jens Christoffers ◽  
Mathias S. Wickleder
Keyword(s):  
Nucleophilic Aromatic Substitution ◽  
Electrophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Nucleophilic Substitutions ◽  
Sulfonic Acids ◽  
Subsequent Oxidation ◽  
Aromatic Substrates ◽  
Diazonium Ions ◽  
Metal Organic

Oligosulfonic acids are promising linker compounds for coordination polymers and metal-organic frameworks, however, compared to their carboxylic acid congeners, often not readily accessible by established synthetic routes. This Account highlights the synthesis of recently developed aromatic and aliphatic di-, tri- and tetrasulfonic acids. While multiple electrophilic sulfonations of aromatic substrates are rather limited, the nucleophilic aromatic substitution including an intramolecular variant, the Newman–Kwart rearrangement, allows the flexible introduction of up to four sulfur-containing moieties at an aromatic ring. Sulfonic acids are then accessed by oxidation of thiols, thioethers, or thioesters either directly with hydrogen peroxide or in two steps with chlorine (generated in situ from N-chlorosuccinimide/hydrochloric acid) to furnish sulfochlorides which are subsequently hydrolyzed. In the aliphatic series, secondary alcohols as starting materials are converted into thioethers, thioesters, or thiocarbonates by nucleophilic substitutions, which are also subsequently oxidized to furnish sulfonic acids.1 Introduction2 Electrophilic Aromatic Substitution3 Nucleophilic Aromatic Substitution3.1 Intermolecular SNAr3.2 Intermolecular with Subsequent Oxidation3.3 Intramolecular with Subsequent Oxidation4 Nucleophilic Aliphatic Substitution with Subsequent Oxidation5 Oxidation5.1 Oxidation of Thiocarbonates5.2 Oxidation of Thioethers5.3 Oxidation of Thioesters6 Thermolysis of Neopentylsulfonates7 Functionalization via Diazonium Ions8 Conclusion

A 15N, 13C, and 1H NMR study of reaction products from arylguanidines and chloroformate esters

1991 ◽  
Vol 56 (7) ◽  
pp. 1505-1511 ◽  
Author(s):  
Antonín Lyčka ◽  
Karel Palát
Keyword(s):  
1H Nmr ◽  
Nmr Spectra ◽  
Reaction Products ◽  
H Nmr ◽  
Nmr Study

The 15N, 13C, and 1H NMR spectra of the reaction products from arylguanidines with two mols of chloroformate esters have been measured. With application of the corresponding 15N isotopomer it has been proved that the reaction products have the structures IIIa-IIIc.

scholarly journals Tautomerisation in 1-(4-Methylphenylazo)naphthalen-2-ol and 2-(4-Methylphenylazo)-4-methylphenol: A Crystallographic and 13C{1H}NMR Study

1999 ◽  
Vol 23 (3) ◽  
pp. 178-179
Author(s):  
Wendy I. Cross ◽  
Kevin R. Flower ◽  
Robin G. Pritchard
Keyword(s):  
Acetic Acid ◽  
Nmr Spectroscopy ◽  
Resonant Frequency ◽  
X Ray Diffraction ◽  
X Ray ◽  
H Nmr ◽  
Nmr Study ◽  
Acetic Acid Esters ◽  
Acid Esters ◽  
Equivalent Carbon

The acetic acid esters of 1-(4-methylphenylazo)naphthalen-2-ol 1 and 2-(4-methylphenylazo)-4-methylphenol 3 are prepared and characterised by single crystal X-ray diffraction studies and 13C{1H}NMR spectroscopy; the position of the C(2)13C resonance for the ester is used to predict the position of resonant frequency of the equivalent carbon in the parent alcohols and hence, calculate the position of the azo-hydrazone equilibrium in these compounds.

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