10112-13-7Relevant articles and documents
Electron-withdrawing substituents decrease the electrophilicity of the carbonyl carbon. An investigation with the aid of 13C NMR chemical shifts, v(C=O) frequency values, charge densities, and isodesmic reactions to interprete substituent effects on reactivity
Neuvonen, Helmi,Neuvonen, Kari,Koch, Andreas,Kleinpeter, Erich,Pasanen, Paavo
, p. 6995 - 7003 (2002)
13C NMR chemical shifts and v(C=O) frequencies have been measured for several series of phenyl-or acyl-substituted phenyl acetates and for acyl-substituted methyl acetates to investigate the substituent-induced changes in the electrophilic character of the carbonyl carbon. Charge density, bond order, and energy calculations have also been performed. The spectroscopic and charge density results indicate that opposite to the conventional thinking, electron-withdrawing substituents do not increase the electrophilicity of the carbonyl carbon but instead decrease it. On the other hand, reaction energies of the isodesmic reactions designed show that electron-withdrawing substituents destabilize the carbonyl derivatives investigated. So, a significant ground-state destabilization of carboxylic acid esters, and carbonyl compounds in general, due to the decreased resonance stabilization, is proposed as a novel concept to explain both the increase in their reactivity and the changes in the chemical shifts and carbonyl frequencies induced by electron-withdrawing substituents.
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Shawali,A.S.A.S.,Biechler,S.S.
, p. 3020 - 3026 (1967)
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METHOD FOR PRODUCING CARBONATE COMPOUND AND METHOD FOR PRODUCING AROMATIC POLYCARBONATE
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Paragraph 0190-0192, (2015/06/10)
The present invention relates to a method for producing a carbonate compound containing: a first step of reacting a compound represented by the following Formula (1) with a compound represented by the following Formula (21) or a compound represented by the following Formula (22) to obtain a reaction mixture containing a carbonate compound, and a second step of bringing the reaction mixture containing a carbonate compound into contact with a strongly basic compound, in which R1 represents a monovalent organic group, and R2 represents a divalent organic group.
Polysulfonylamines, XIII. N-Acylonium Salts of Dimesylamine: Synthesis and Mass Spectra
Blaschette, Armand,Linoh, Karin,Safari, Firouz,Schiebel, Hans-Martin
, p. 1639 - 1646 (2007/10/02)
N-Acyl dimesylamines, like acyl chlorides, react with 4-dimethylaminopyridine and other tertiary nitrogen bases to give either solid N-acylonium dimesylaminides (1-3), or onium dimesylaminides (e. g. 4) originating from ketene elimination (eq. (5)).The expected acyl transfer properties of N-acylonium dimesylaminides are confirmed by reactions of 1a with phenol, 4-nitrophenol, p-thiocresol, and N-methylaniline, and of 1b with phenol, resulting in O-, S-, or N-acylation, respectively.With exception of compounds 1b and 3, all dimesylaminides could be characterized by their cation and anion mass spectra using field desorption, secondary ion mass spectrometry or fast atom bombardment. - Keywords: Reaction of N-Acyl Dimesylamines with Nitrogen Bases, Preparation of N-Acylonium Dimesylaminides, Acylation, Ketene Formation, Mass Spectra
