title: A vinylic Rosenmund-von Braun reaction: practical synthesis of acrylonitriles.
abstract: An efficient system based on acetone cyanohydrin and catalytic amounts of copper(I) iodide and 1,10-phenanthroline is reported for the cyanation of alkenyl iodides. A wide range of polysubstituted acrylonitriles could be obtained in fair to good yields and with complete retention of the geometry of the double bond. This extension of the Rosenmund-von Braun reaction also enabled a straightforward formal synthesis of the naturally occurring acrylonitrile alliarinoside.
authors.affiliation: Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques, Université Libre de Bruxelles, Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels, Belgium. gevano@ulb.ac.be.
authors.forename: Alexandre
authors.initials: A
authors.lastname: Pradal
authors.forename: Gwilherm
authors.initials: G
authors.lastname: Evano
mesh_terms: D000181:Acrylonitrile / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry; D007454:Iodides / Q000737:chemistry; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry; D010618:Phenanthrolines / Q000737:chemistry
chemical_list: D001688:Biological Products; D005960:Glucosides; D007454:Iodides; D009570:Nitriles; D010618:Phenanthrolines; C430148:alliarinoside; D003300:Copper; C010833:acetone cyanohydrin; D000181:Acrylonitrile; C025205:1,10-phenanthroline