61589-64-8Relevant articles and documents
Syntheses of fluorous propenes from 3-perfluoroalkyl-2-iodo-1-propanols
Szíjjártó, Csongor,Ivanko, Peter,Takács, Ferenc T.,Szabó, Dénes,Rábai, József
, p. 386 - 389 (2008/12/21)
3-(Perfluoroalkyl)-1-propenes are obtained in excellent yields up to 100-g quantities by deiodination-dehydroxylation reactions of the easily accessible 2-iodo-3-(perfluoroalkyl)-propanols with red phosphorus and catalytic amounts of iodine or with an SnCl2/POCl3 reagent pair in pyridine (fluorous Cornforth reaction). Both methods afford fluorous propenes in high GC purity, the former one has high atom-economy and proceeds safely if the fluorous iodohydrin precursors are added in increments; for the solid ones using a 'hot-melt' dropping funnel. The title fluorous propenes are effectively isolated by co-distillation with pyridine.
Reaction of Perfluoroalkanesulfinates with Allyl and Propargyl Halides. A Convenient Synthesis of 3-(Perfluoroalkyl)prop-1-enes and 3-(Perfluoroalkyl)allenes
Hu, Chang-Ming,Qing, Feng-Ling,Huang, Wei-Yuan
, p. 2801 - 2804 (2007/10/02)
The reaction of perfluoroalkanesulfinates, RfCF2SO2Na, with allyl and propargyl halides, in the presence of (NH4)2S2O8, gave 3-(perfluoroalkyl)prop-1-enes (RfCH2CH=CH2) and 3-(perfluoroalkyl)allenes (RfCH=C=CH2), respectively, in good yield.Evidence is presented for a radical addition-elimination mechanism for the reaction.The reaction represents a synthetically viable and convenient route to such compounds.