Synthesis and properties of O-vinylamidoximes

Authors
Trofimov, BA Schmidt, EY Vasil'tsov, AM Mikhaleva, AI Zaitsev, AB Morozova, LV Gorshkov, AG Henkelmann, J Arndt, JD
Citation
Ba. Trofimov et al., Synthesis and properties of O-vinylamidoximes, SYNTHESIS-S, (16), 2001, pp. 2427-2430
Citations number
16
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
SYNTHESIS-STUTTGART
ISSN journal
00397881 → ACNP
Issue
16
Year of publication
2001
Pages
2427 - 2430
Database
ISI
SICI code
0039-7881(200112):16<2427:SAPOO>2.0.ZU;2-D
Abstract
O-Vinylamidoximes 2 are synthesized from amidoximes 1 and acetylene in supe rbase systems (KOH/DMSO, KOH/NMP, NaOH/CsF/NMP) in a preparative yield of u p to 80%. They decompose explosively above 150 degreesC, being resistant to solvolysis in the KOH/DMSO system (100 degreesC, 3 h) and to polymerizatio n (AIBN, UV). Trifluoroacetylation of O-vinylbenzamidoxime 2b with (CF3CO)( 2)O/pyridine gives 5-trifluoromethyl-3-phenyl-1,2,4-oxadiazole (3) in 49% y ield.