title: From alpha-carbamoyl-alpha-cyanooxiranes to 3-halogenopyruvamides.
abstract: The crystal structures of the first stable alpha-diol from the alpha-halogenopyruvamide series, 3-chloro-2, 2-dihydroxy-3-phenylpropanamide, C(9)H(10)ClNO(3), and three products [3-(4-chlorophenyl)-2-cyano-2,3-epoxypropanamide, C(10)H(7)ClN(2)O(2), 3-bromo-2-cyano-2-hydroxy-3-p-tolylpropanamide, C(11)H(11)BrN(2)O(2), 3-bromo-2-oxo-3-p-tolylpropanamide, C(10)H(10)BrNO(2)] obtained during the systematic synthesis of alpha-halogenopyruvamides are reported. The crystal structures are dominated by hydrogen bonds involving an amide group. The stability of the geminal diol could be ascribed to hydrogen bonds which involve both hydroxyl groups.
authors.affiliation: Faculty of Chemistry and Chemical Technology, University of Ljubljana, Askerceva 5, PO Box 537, SI-1001 Ljubljana, Slovenia. nina.lah@uni-lj.si
authors.forename: N
authors.initials: N
authors.lastname: Lah
authors.forename: I
authors.initials: I
authors.lastname: Leban
authors.forename: A
authors.initials: A
authors.lastname: Majcen-Le Maréchal
authors.forename: P
authors.initials: P
authors.lastname: Le Grel
authors.forename: A
authors.initials: A
authors.lastname: Robert
authors.forename: J
authors.initials: J
authors.lastname: Sieler
authors.forename: G
authors.initials: G
authors.lastname: Giester
mesh_terms: D018360:Crystallography, X-Ray; D004852:Epoxy Compounds / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D009570:Nitriles / Q000737:chemistry*; D010667:Phenylpyruvic Acids / Q000737:chemistry*; D011773:Pyruvates / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D004852:Epoxy Compounds; D009570:Nitriles; D010667:Phenylpyruvic Acids; D011773:Pyruvates