REGIOSELECTIVE RING-OPENING OF 3-ARYL-2-CYANO-2-(METHOXYCARBONYL)OXIRANES WITH METAL-HALIDES AND SILICA-GEL-SUPPORTED METAL-HALIDES - SYNTHESIS OF SUBSTITUTED BUT-3-EN-4-OLIDES

Authors
BRINE N FOUCAUD A
Citation
N. Brine et A. Foucaud, REGIOSELECTIVE RING-OPENING OF 3-ARYL-2-CYANO-2-(METHOXYCARBONYL)OXIRANES WITH METAL-HALIDES AND SILICA-GEL-SUPPORTED METAL-HALIDES - SYNTHESIS OF SUBSTITUTED BUT-3-EN-4-OLIDES, Bulletin de la Societe chimique de France, 130(5), 1993, pp. 620-624
Citations number
27
Categorie Soggetti
Chemistry Inorganic & Nuclear",Biology,Chemistry
Journal title
Bulletin de la Societe chimique de France → ACNP
ISSN journal
00378968
Volume
130
Issue
5
Year of publication
1993
Pages
620 - 624
Database
ISI
SICI code
0037-8968(1993)130:5<620:RRO3>2.0.ZU;2-Z
Abstract
Regioselective ring opening of 3-aryl-2-cyano-2-(methoxyarbonyl)oxiran es 1 with transition metal halides (copper (II) chloride. copper (11) bromide, zinc bromide, cobalt chloride and ferric chloride) and silica -gel-supported metal halides gave methyl 3-aryl-2-cyano-3-halo-2-hydro xypropanoates 5, 6 and methyl 3-aryl-3-halo-2-oxopropanoates 2, 3. The reaction of 1 iii chlorobenzene under reflux with silica-gel-supporte d copper (II) halides gave but-3-en-4-olides 4.