title: Double anionic cycloaromatization of 2-(6-substituted-3-hexene-1,5-diynyl)benzonitriles initiated by methoxide addition.
abstract: [reaction: see text] Treatment of 2-((3Z)-undecene-1,5-diynyl)benzonitrile with 5 equiv of sodium methoxide in refluxing methanol for 16 h gave 1-pentyl-6-methoxyphenanthridine in 12% yield, 1-pentyl-6-phenanthridone in 6% yield, and 2-(2-pentyl-6-methoxyphenyl)benzonitrile in 4% yield. Under the same reaction conditions, methanolysis of several other benzonitriles gave similar results. Phenanthridine and biphenyl derivatives were obtained as the major products. A mechanism for this novel cycloaromatization reaction of enediynes is proposed.
authors.affiliation: School of Chemistry, Kaohsiung Medical College, Kaohsiung, Taiwan. mijuwu@cc.kmc.edu.tw
authors.forename: M J
authors.initials: MJ
authors.lastname: Wu
authors.forename: C F
authors.initials: CF
authors.lastname: Lin
authors.forename: S H
authors.initials: SH
authors.lastname: Chen
mesh_terms: D003500:Cyclization; D006841:Hydrocarbons, Aromatic / Q000138:chemical synthesis; D007202:Indicators and Reagents; D009570:Nitriles / Q000138:chemical synthesis*
chemical_list: D006841:Hydrocarbons, Aromatic; D007202:Indicators and Reagents; D009570:Nitriles; C014356:benzonitrile