Journal ArticleDOI
Darstellung und Eigenschaften mesoionischer Oxazolone
TLDR
In this article, the synthesis and spectral properties of 3-methyl-2,4-diaryloxazolium 5-oxides (2, 16-21) are described.Abstract:
Die Synthese und die spektralen Eigenschaften sydnon-analoger 3-Methyl-2.4-diaryl-oxazolium-5-oxide (2, 16–21) werden beschrieben. Die Thermolyse von 2 fuhrt zu einem tetra-substituierten Allen, das vielleicht durch Dimerisation eines mit 2 valenztautomeren Ketens (28) und Kohlendioxid-Abspaltung gebildet wird. Bei der Offnung des Oxazolium-oxid-Ringes mit Verbindungen HX greift das Nucleophil an der Carbonylgruppe an. Auch uber den Verlauf der Autoxydation von 2 werden Aufschlusse erzielt.
Preparation and Properties of Mesoionic Oxazolones
Synthesis and spectral properties of 3-methyl-2,4-diaryloxazolium 5-oxides (2, 16–21) are described. The thermolysis of 2 affords a tetrasubstituted allene; possibly this is the result of a dimerization of the ketene 28 which is a valence tautomer of 2, and elimination of carbon dioxide. In the ring opening of oxazolium 5-oxides with compounds HX the nucleophile attacks the carbonyl group. Also the course of autoxidation of 2 was investigated.read more
Citations
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Journal ArticleDOI
1,5-Elektrocyclisierungen – ein wichtiges Prinzip der Heterocyclen-Chemie†
TL;DR: In this paper, anioncharakters and ringoffnungen in the Hetero-Reihe eignet sich as Ordnungsprinzip.
Journal ArticleDOI
1.3‐Dipolare Cycloadditionen, LVI. Eine bequeme Synthese von N‐substituierten Pyrrolen aus mesoionischen Oxazolonen und Alkinen
TL;DR: In this paper, a convenient synthesis of N-substituted Pyrroles from Mesoionic Oxazolones and Alkynes has been presented, which can be used for cycloadditions if one treats them with acetic anhydride in the presence of suitable acetylenic dipolarophiles.
Journal ArticleDOI
The Development of a Catalytic Synthesis of Münchnones: A Simple Four-Component Coupling Approach to α-Amino Acid Derivatives
TL;DR: A new palladium-catalyzed route to prepare 1,3-oxazolium-5-oxides directly from imine, carbon monoxide, and acid chloride building blocks has been developed, providing a straightforward catalytic synthesis of Münchnones and is amenable to generating a diverse range of products by simple modification of the imine or acid chloride starting materials.
Book ChapterDOI
Heterocyclic Mesomeric Betaines and Analogs in Natural Product Chemistry. Betainic Alkaloids and Nucleobases
TL;DR: In this article, the authors reviewed the distinct classes of heterocyclic mesomeric betaines and analogs in natural product chemistry, including mesoion and N-oxide.
Journal ArticleDOI
The Use of Carbon Monoxide and Imines as Peptide Derivative Synthons: A Facile Palladium‐Catalyzed Synthesis of α‐Amino Acid Derived Imidazolines
TL;DR: One of the most facile routes to prepare carboxylate-substituted imidazolines is by the palladium-catalyzed coupling of an imine, carbon monoxide, and an acid chloride.
References
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Journal ArticleDOI
Intensities and Shapes of Infrared Absorption Bands of Substances in the Liquid Phase
Journal ArticleDOI
Regel zur Abschätzung der chemischen Verschiebung von Protonen an einer Doppelbindung
Journal ArticleDOI
Meso-ionic compounds
Wilson Baker,W. D. Ollis +1 more
TL;DR: In this article, the currently known types of meso-ionic heterocycles, which can then be considered in relation to the total number of possibilities associated with certain structural conditions.
Journal ArticleDOI
Die Addukte primärer und sekundärer Amine an Carbonester der Acetylenreihe und ihre Konfiguration
TL;DR: Aus Propiolsaure-methylester und prim. Aminen entstehen cis-and trans-3-Amino-acrylsauremethyleter; im Gleichgewicht bevorzugt ist das cis-Isomere mit intramolekularer H-Brucke as discussed by the authors.