Abstract
Treatment of a vinyl chloride with commercially available aqueous sodium hypochlorite solution in a 2:5 mixture of acetic acid/acetone at 0 °C for about 1 h cleanly leads to the corresponding α-chloroketone. Similarly, if a vinyl bromide is exposed to sodium hypobromite (freshly prepared from bromine and sodium hydroxide) at 0 °C in 2:5 acetic acid/acetone as solvent, an α-bromoketone is produced. This methodology has been applied to a number of vinyl chlorides and vinyl bromides, and the transformations generally proceed in high yields. The mild reaction conditions are compatible with a variety of functional groups including amides, esters, and imines.
Original language | English (US) |
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Pages (from-to) | 3323-3326 |
Number of pages | 4 |
Journal | Journal of Organic Chemistry |
Volume | 68 |
Issue number | 8 |
DOIs | |
State | Published - Apr 18 2003 |
All Science Journal Classification (ASJC) codes
- Organic Chemistry