The adjacency of a perfluoroalkyl group can affect the stability of intermediate reaction products in such an adverse way as to render impractical some conventional reactions. Aldehydes and ketones 80 fluorinated react with diazomethane to give the expected oxides, but these are cleaved by hydrogen to give secondary and tertiary alcohols, instead of primary and secondary alcohols. Pyrolysis of N, N'-di (trifluoroacety1) hydrazine and N- ...
[Jansen, Michael P.; Koshy, Kalavelil M.; Mangru, Nevindra N.; Tidwell, Thomas T. Journal of the American Chemical Society, 1981 , vol. 103, # 13 p. 3863 - 3867]
