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.
- allylic alcohols
Brown, S. J., Corr, S., & Percy, J. (2000). Fluorinated succinic acid derivatives from new refrigerants via ozonolysis of haloalkenes. Tetrahedron Letters, 41(27), 5269-5273 . https://doi.org/10.1016/S0040-4039(00)00804-2