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Cycloadditions of nitrile oxides to amidoximes. A general synthesis of 3,5-disubstituted 1,2,4-oxadiazole-4-oxides.

โœ Scribed by Paolo Quadrelli; Anna Gamba Invernizzi; Mario Falzoni; Pierluigi Caramella


Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
578 KB
Volume
53
Category
Article
ISSN
0040-4020

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๐Ÿ“œ SIMILAR VOLUMES


Dipolar addition reactions of nitrile ox
โœ P. Rajagopalan ๐Ÿ“‚ Article ๐Ÿ“… 1969 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 127 KB

We would like to report that aliphatic and aromatic nitrile oxides (I), as exemplified by pivalonitrile oxide and I-chlorobenzonitrile oxide respectively, react with methyl imidates (II) at room temperature (in absolute ether) to yield 1.2,4-oxadiazoles of the type III (See Table ).

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The well established high synthetic utility of 2?-isoxazolines is due to their synthetic equivalency of a wide variety of important functionalized building blocks such as P-hydroxy ketones+ fi-amino alcohols, cr,punsaturated ketones, and related functionalities.' Nitrile oxide cyclctaddition offers

A thermal fragmentation of 1,2,4-oxadiaz
โœ P Quadrelli; G Campari; M Mella; P Caramella ๐Ÿ“‚ Article ๐Ÿ“… 2000 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 134 KB

1,2,4-Oxadiazole-4-oxides undergo clean thermal cleavage in refluxing chlorobenzene or xylene to nitriles and nitrosocarbonyl intermediates, which are either trapped with suitable olefins to afford ene adducts or dimerize and rearrange to anhydrides.