Conversion of bromoalkenes into alkynes by wet tetra-n-butylammonium fluoride.
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.
Okutani
Masaru
M
Faculty of Pharmacy, Meijo University, 150 Yagotoyama, Tempaku-ku, Nagoya 468-8503, Japan.
Mori
Yuji
Y
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
D000475:Alkenes; D000480:Alkynes; D006842:Hydrocarbons, Brominated; D000644:Quaternary Ammonium Compounds; C009405:tetrabutylammonium