title: Conversion of bromoalkenes into alkynes by wet tetra-n-butylammonium fluoride.
abstract: Tetra-n-butylammonium fluoride was found to be a mild and efficient base for the elimination reaction of bromoalkenes. Treatment of 1,1-dibromoalkenes, (Z)-1-bromoalkenes, and internal bromoalkenes with 5 equiv of TBAF x 3H2O in DMF yielded terminal and internal alkynes in high yields without undue regard to the presence of water.
authors.affiliation: Faculty of Pharmacy, Meijo University, 150 Yagotoyama, Tempaku-ku, Nagoya 468-8503, Japan.
authors.forename: Masaru
authors.initials: M
authors.lastname: Okutani
authors.forename: Yuji
authors.initials: Y
authors.lastname: Mori
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D000480:Alkynes; D006842:Hydrocarbons, Brominated; D000644:Quaternary Ammonium Compounds; C009405:tetrabutylammonium