355-30-6Relevant articles and documents
SnX2/Al-promoted formylation of per(poly)fluoroalkyl halides with N,N-dimethylformamide
Hu, Chang-Ming,Chen, Jian
, p. 189 - 192 (1994)
In the presence of catalytic amounts of stannous salts (20 molpercent) and aluminium powder, per(poly)fluoroalkyl iodides or bromides react smoothly with DMF under mild conditions to give the corresponding per(poly)fluoroalkyl aldehydes in good to excellent yield.A tin-containing intermediate was obtained.A possible mechanism is proposed.
Organofluorine compounds and fluorinating agents part 17: Sonochemical-forced preparation of perfluoroalkanals and their use for non-conventional acetalations of carbohydrates 1, 2
Miller, Alexey O.,Peters, Dietmar,Zur, Cornelia,Frank, Michael,Miethchen, Ralf
, p. 33 - 38 (2007/10/03)
The homologous 1-iodo-perfluoroalkanes 1a-1c and α,ω-dibromo-perfluoroalkanes 4a, 4b were carbonylated with DMF in the presence of Al/SnCl2 or Al/PbBr2 under sonication in a short reaction time. The hydrated aldehydes 2a-2c and 5a, 5b respectively were obtained in good yields allowing dehydration to 3a-3c and 6a, 6b. Some of the fluorinated aldehydes were selected as substrates in a Wittig-Horner olefination assisted by ultrasound and in non-conventional acetalations of methyl α-L-rhamnopyranoside (9). Thus, (E)-1-perfluorooctyl-2-phenylsulphonyl-ethene (8) was prepared from 3c and the phosphonate 7 by Wittig-Horner synthesis. Acetalations of 9 were carried out with the aldehydes (3a, 3b, 6a), hydrated aldehydes (2a, 2b), and the aldehyde hemiacetal 12 respectively, in the presence of dicyclohexylcarbodiimide (DCC). In all cases, a selective epimerization was observed at the C-atom 3 of the monosaccharide, i.e. polyfluoroalkylidenated 6-deoxy-α-L-altropyranosides 10, 11, 13, and 14 were obtained.