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C-Glycosides V: Données mécanistiques sur l'halogénation d'hydrazones et d'oximes dérivées de sucres. Communication préliminaire

✍ Scribed by J. M. J. Tronchet; Br. Baehler; N. Le-Hong; P. F. Livio


Publisher
John Wiley and Sons
Year
1971
Tongue
German
Weight
386 KB
Volume
54
Category
Article
ISSN
0018-019X

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✦ Synopsis


Abstract

The bromination of aldehydo‐sugars p‐nitrophenylhydrazones has been studied and the gem‐bromo‐azo intermediates isolated and characterized in some cases. In the same way, in the chlorination of aldehydo‐sugars oximes gem‐chloro‐nitroso intermediates have been obtained and in some instances isolated. These observations support a S~E~2′ mechanism for such reactions.


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## Abstract The syntheses of three types of sugar nitrones (aldonitrone, ketonitrone and α‐β unsaturated aldonitrone) are described. On 1,3‐dipolar cycloaddition with phenylacetylene, the aldonitrone gave two Δ~4~‐isoxazolines epimeric at the new asymetric carbon, while the same reaction on the ket