✦ LIBER ✦

Fragmentation of nitrile oxides with triethylamine

✍ Scribed by P. Caramella; A. Corsaro; A. Compagnini; F. Marinone Albini

Publisher: Elsevier Science
Year: 1983
Tongue: French
Weight: 246 KB
Volume: 24
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)88346-x

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✦ Synopsis

The tormation of 1,2,4-oxadiazoles is frequently observed as a side reaction in cycle additions with nitrile oxides generated in situ and follows from a fragmentation induced by Et3N. This latter is oxidized to N,N-diethylvinylamine, which is trapped as a cycloadduct. 4litrile oxides are usually generated in situ from suitable precursors. Dehydrohalogenation of the stable and storable hydroximic acid chlorides with triethylamine in an inert solvent is a very efficient entry to nitrile oxides and the procedure has gained general acceptance for cg cloaddition purposes3. While active dipolarophiles afford very good yields -almost quantitative -of cycloadducts 1, with lower reactive dipolarophiles the normal decay of nitrile oxides, i.e. the dimerization to furoxan 2, competes. In addition, however, noteworthy amounts of 1,2,4 -oxadiazole 1. were observedl.

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