A facile preparation of gem-difluorohomoallylic alcohols[1]
β Scribed by Zhen-Yu Yang; Donald J. Burton
- Publisher
- Elsevier Science
- Year
- 1989
- Tongue
- English
- Weight
- 209 KB
- Volume
- 44
- Category
- Article
- ISSN
- 0022-1139
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β¦ Synopsis
The reaction of 3-bromo-3,3-difluoropropene with zinc powder in THF at OΒ°C to room temperature in the presence of aldehydes and ketones provides a useful, easily scaled up route to gemdifluorohomoallylic alcohols. a,P-Unsaturated aldehydes and ketones give exclusively the 1,2-addition product. In all cases, only the a-gem-difluorohomoallyl regioisomer was observed.
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The method described by Makosza and Wawrzyniewicz 1,2,3 is a most useful addition to the arsenal of dihalocarbene-generating reactions4. The two-phase reaction system consisting of the olefins, chloroform, and 50% aqueous sodium hydroxide with a tetraalkylammonium chloride as catalyst provides a par