59974-27-5Relevant articles and documents
Halofluorination of alkenes using trihaloisocyanuric acids and HF-pyridine
Crespo, Livia T. C.,Ribeiro, Rodrigo Da S.,De Mattos, Marcio C. S.,Esteves, Pierre M.
experimental part, p. 2379 - 2382 (2010/09/04)
Halofluorination of alkenes with a new system (trihaloisocyanuric acids and HF-pyridine) results in the formation of vicinal halofluoroalkanes. The reaction is regioselective leading to Markovnikov-oriented products and the halofluorinated adducts follow anti-addition in the case of cyclohexene and 1-methylcyclohexene. Reaction yields range from 67-88%. Georg Thieme Verlag Stuttgart · New York.
A mild method for halofluorination of alkenes with ionic liquid EMIMF(HF)2.3
Yoshino, Hideaki,Matsubara, Seijiro,Oshima, Koichiro,Matsumoto, Kazuhiko,Hagiwara, Rika,Ito, Yasuhiko
, p. 121 - 123 (2007/10/03)
Halofluorination of alkene in the presence of N-halosuccinimide and ionic liquid, 3-ethyl-1-methyl-imidazorium oligo hydrogen fluoride (EMIMF(HF) 2.3), as a HF source was demonstrated. Various alkenes were converted into β-halo organofluorides
Synthesis of a fluorinated ether lipid analogous to a platelet activating factor
Haufe, Guenter,Burchardt, Annegret
, p. 4501 - 4507 (2007/10/03)
The synthesis of racemic 2-fluoro-3-hexadecyloxy-2-methyl-prop-1-yl 2′-(trimethylammonio)ethyl phosphate (10), a fluorinated analogue of the anticancer active and blood platelet activating ether lipids 8 and 9, has been achieved in a six-step sequence from methallyl alcohol (11). Etherification of 11 with hexadecyl bromide gave allylic ether 12, bromofluorination of which afforded the bromo-substituted fluoride 13, which was subsequently transformed into the acetate 14. Hydrolysis of 14 gave the key intermediate 2-fluoro-2-(hexadecyloxymethyl)propanol (15), which was attached to the phosphocholine residue in the final step. Enzyme-catalyzed deracemization of the fluorohydrin 15 by acetylation with several lipases gave optically active compounds 14 and 15, with a maximum ee of 61% for 15 with Candida antarctica lipase catalysis after 74% conversion. An enantioselective synthesis of 10, based on a planned eight-step synthesis starting from α-methylstyrene, failed. The anticancer activity of racemic 10 has been observed in an in vivo model of methylcholanthrene-induced mouse fibrosarcoma.
