Efficient carbonyl addition of polyfluorochloroethyl, -ethylidene, and -ethenyl units by means of 1,1,1-trichloro-2,2,2-trifluoroethane and zinc.
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Thermally stable zinc carbenoid CF<SUB>3</SUB>CCl<SUB>2</SUB>ZnCl was prepared from 1,1,1-trichloro-2,2,2-trifluoroethane and zinc powder in <I>N</I>,<I>N</I>-dimethylformamide and was allowed to add to carbonyls of aldehydes and α-keto esters in excellent yields to give 1-substituted 2,2-dichloro-3,3,3-trifluoro-1-propanols. Employment of excess zinc induced further reductive β-elimination to afford 1-substituted 2-chloro-3,3,3-trifluoropropenes (<B>3</B>) and 1-substituted 2-chloro-3,3-difluoro-2-propen-1-ols (<B>4</B>). Exclusive formation of <B>3</B> was achieved by use of acetic anhydride as the co-reagent, whereas <B>4</B> was produced with an aluminium chloride catalyst highly selectively.
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