Gem-Difluoroallyllithium: Preparation by the Transmetalation Procedure and some Reactions.
MASSACHUSETTS INST OF TECH CAMBRIDGE DEPT OF CHEMISTRY
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3,3-Difluoroallyltrimethyltin has been prepared by the reaction of beta-trimethylstannylethylidenetriphenylphosphorane with chlorodifluoromethane. This tin compound reacts with n-butyllithium in tetrahydrofuran at -95 C to generate gem-difluoroallyllithium. The latter, however, is not stable in solution at that temperature. If generated in situ in the presence of a triorganochlorosilane, products of type R3SiCF2CH-CH2 are obtained in good yield. Addition to the CO bond of 3-pentanone to give C2H52COHCF2CHCH2 was achieved by the method of altnerate, incremental additions. Author
- Organic Chemistry