- Syntheses of fluorous propenes from 3-perfluoroalkyl-2-iodo-1-propanols
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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.
- Szíjjártó, Csongor,Ivanko, Peter,Takács, Ferenc T.,Szabó, Dénes,Rábai, József
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p. 386 - 389
(2008/12/21)
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- Synthese de 3-perfluoroalkylprop-1-enes RF-CH2-CH=CH2
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The reactions of perfluoroalkyl iodides with allylbromide or chloride, in the presence of solid potassium hydroxide KOH give 3-perfluoroalkylprop-1-enes RFCH2CH=CH2 in good yields under mild conditions. This reaction represents a synthetically viable and convenient route to such compounds.
- Rubio,Blancou,Commeyras
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p. 171 - 175
(2007/10/03)
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- Reaction of Perfluoroalkanesulfinates with Allyl and Propargyl Halides. A Convenient Synthesis of 3-(Perfluoroalkyl)prop-1-enes and 3-(Perfluoroalkyl)allenes
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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.
- Hu, Chang-Ming,Qing, Feng-Ling,Huang, Wei-Yuan
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p. 2801 - 2804
(2007/10/02)
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- REACTIONS OF RfI(Ph)OSO2CF3 WITH ALKENES AND ALKADIENES
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A successful cationic perfluoroalkylation of alkenes and alkadienes with RfI(Ph)OSO2CF3 was described.The reactivity of RfI(Ph)OSO3H was also examined.
- Umemoto, Teruo,Kuriu, Yuriko,Nakayama, Shin-ichi
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p. 1169 - 1172
(2007/10/02)
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