title: Reaction of olefins with nitriles under solvent-free conditions using molecular iodine as a catalyst in the presence of water.
abstract: The reaction of olefins with nitriles using iodine as a catalyst under solvent-free conditions was investigated. The reaction of cycloolefins, such as cyclopentene and cyclohexene, with benzonitrile using iodine as a catalyst produced both amide and heterocyclic compounds. The reaction of chiral (+)-camphene with benzonitrile produced racemic (±)-N-isobornylbenzamide (N-((1S,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl)benzamide). This indicated that skeletal rearrangement of camphene as well as amidation occurred. The optimized conditions were determined to be as follows: temperature, 90°C; molar ratio of nitrile:alcohol:iodine:water, 1:5:0.2:1.0; and reaction time, 18 h. The yield was 87% under these conditions. The reaction of (+)-camphene also proceeded with the other aromatic and aliphatic nitriles to produce racemic isobornylamides. However, except for styrene, complex reactions occurred in the reactions of benzonitrile with other terpenic olefins.
authors.affiliation: Education Center, Faculty of Engineering, Chiba Institute of Technology, Chiba, Japan.
authors.forename: Yohko
authors.initials: Y
authors.lastname: Hanzawa
authors.forename: Yoshio
authors.initials: Y
authors.lastname: Kasashima
authors.forename: Kazuki
authors.initials: K
authors.lastname: Tomono
authors.forename: Takashi
authors.initials: T
authors.lastname: Mino
authors.forename: Masami
authors.initials: M
authors.lastname: Sakamoto
authors.forename: Tsutomu
authors.initials: T
authors.lastname: Fujita
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D007455:Iodine / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry*
chemical_list: D000475:Alkenes; D009570:Nitriles; D014867:Water; D007455:Iodine