ISSN:
0009-2940
Keywords:
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Iminophosphoran-vermittelte Syntheses von mesoionischen 1,3,4- Oxadiazolo[3,2a]pyridinylium-2-aminidenDas Iminophosphoran 2 reagiert mit Methylisocyanat zu dem mesoionischen 1,3,4-Oxadiazolo[3,2-a]pyridinylium-2-methylaminid 3, das durch CF3SO3CH3 zum 1,3,4-Oxadiazolo[3,2-a]-pyridinium-Kation 4 methyliert wird. Struktur 4 wurde durch Röntgenstrukturanalyse gesichert. Durch Einwirkung von Base lagert das mesoionische Aminid 3 zum isomeren mesoionischen 1,3,4-Triazolo[3,2-a]pyridinylium-2-olat 11 um. Verbindung 3 wird durch (Arylimino)triphenylphosphorane in die entsprechenden 1,3,4-Oxadiazolo[3,2-a]pyridinium-2-arylaminide 12 umgewandelt, die auch aus Iminophosphoran 2 und Hydroximoylchloriden zugänglich sind.
Notes:
Reaction of iminophosphorane 2 with methyl isocyanate yields the mesoionic 1,3,4-oxadiazolo[3,2-a]pyridinylium-2-methylamindie 3, which undergoes N-methylation with CF3SO3CH3 to give the 1,3,4-oxadiazolo[3,2-a]pyridinium cation 4. The structure of compound 4 has been established by means of X-ray crystallography. Mesoionic aminide 3 undergoes rearrangement by the action of base to give the isomeric mesoionic compound 1,3,4-triazolo[3,2-a]pyridinylium-2-olate 11. Compound 3 by the action of (arylimino)triphenylphosphoranes is converted into the corresponding 1,3,4-oxadiazolo[3,2-a]pyridinylium-2-arylaminides 12, which can be also prepared from iminophosphorane 2 and hydroximoyl chlorides.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19881210825
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