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Fluorinated succinic acid derivatives from new refrigerants via ozonolysis of haloalkenes

Brown, Samantha J and Corr, Stuart and Percy, Jonathan (2000) Fluorinated succinic acid derivatives from new refrigerants via ozonolysis of haloalkenes. Tetrahedron Letters, 41 (27). pp. 5269-5273. ISSN 0040-4039

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Abstract

Fluoro- and di-fluoro allylic alcohols obtained from HFC-134a and HCFC-133a were transformed through [3,3]-sigmatropic rearrangements into 3-fluoro-4-halo-4-alkenoates with variable substitution at the 2- and 3-positions. Ozonolysis of the haloalkenes afforded the corresponding acyl halides which could be trapped with nucleophiles to afford fluorinated succinic acid derivatives in which the two carboxylic acid groups were differentiated.