38550-45-7Relevant academic research and scientific papers
Synthesis and characterization of a new class of polyfluorinated alkanes: Tetrakis(perfluoroalkyl)alkane
Gambaretto,Conte,Fornasieri,Zarantonello,Tonei,Sassi,Bertani, Roberta
, p. 57 - 63 (2003)
The synthesis and physico-chemical characterization of 1,1,2,2-tetrakis(perfluoroalkyl-methylene)ethane {[F(CF2)nCH2]2CH}2 (n=6, TK6;n=8, TK8 ) are reported. The synthesis consists of four steps: (1) addition of allyl alcohol to a perfluoroalkyl iodide, F(CF2)nI(n=6,8) to give the corresponding iodo-adduct; (2) dehalogenation of the adduct by treatment with zinc in aqueous acetic acid, yielding 3-perfluoro-n-alkyl-1-propene; (3) addition of 3-perfluoro-n-alkyl-l-propene to perfluoroalkyl iodide, F(CF2)nI (n=6,8) to give 1,3-perfluoro-n-alkyl-2-iodo-propane; (4) coupling of 1,3-perfluoro-n-alkyl-2-iodo-propane by zinc in acetic anhydride giving the final products. TK6 and TK8 are characterized by very low surface tension values and exhibit very good properties as potential ski-waxes.
Addition of RFI (CnF2n+1I; n = 4, 6, 8) to allyl alcohol catalyzed by zinc in different solvents: application to the synthesis of F-alkyl epoxypropanes
Laurent, Philippe,Blancou, Hubert,Commeyras, Auguste
, p. 125 - 128 (1993)
The addition of RFI to allyl alcohol catalyzed by zinc in different solvents has been studied.The adduct RFCH2CHICH2OH readily gives the corresponding F-alkyl epoxypropane.
Regioselective ring opening of [(perfluoroalkyl)methyl] oxiranes with N-nucleophiles
Conte,Maniero,Zaggia,Bertani,Gambaretto,Berton,Seraglia
, p. 1274 - 1280 (2005)
The reactions of C8F17CH2CHCH2O with some primary and secondary aliphatic amines affording selective ring opening at Cβ are reported. The reactions with secondary amines HNR1R2 (R1 = R2 = Et; R1 = But, R2 = CH2CH2O(CO)C(CH 3)CH2; R1 = Et, R2 = CH 2CH2OH; R1 = R2 = CH 2CH2OH) gave the corresponding C8F 17CH2CH(OH)CH2NR1R2 derivatives. For R1 = Et, R2 = CH2CH 2OH; R1 = R2 = CH2CH2OH, the reactions proceed through the selective nucleophilic attack of the NH moiety with no evidence of reactivity of the OH group. The reactions with the primary amines, allylamine and n-hexamethylenediamine, gave different products depending on reaction conditions.
The Different Faces of Photoredox Catalysts: Visible-Light-Mediated Atom Transfer Radical Addition (ATRA) Reactions of Perfluoroalkyl Iodides with Styrenes and Phenylacetylenes
Rawner, Thomas,Lutsker, Eugen,Kaiser, Christian A.,Reiser, Oliver
, p. 3950 - 3956 (2018/05/22)
A photoredox-catalyzed procedure for the iodoperfluoroalkylation of styrenes and phenylacetylenes using readily available copper phenanthroline catalyst is reported. In contrast to commonly employed [Ru(bpy)3]Cl2, [Ru(phen)3/su
Benzophenone vs. Copper/Benzophenone in Light-Promoted Atom Transfer Radical Additions (ATRAs): Highly Effective Iodoperfluoroalkylation of Alkenes/Alkynes and Mechanistic Studies
Beniazza, Redouane,Atkinson, Rachel,Absalon, Christelle,Castet, Frédéric,Denisov, Sergey A.,McClenaghan, Nathan D.,Lastécouères, Dominique,Vincent, Jean-Marc
, p. 2949 - 2961 (2016/09/16)
Iodoperfluooralkylation of terminal alkenes and alkynes is effectively photo-promoted by benzophenone 2 (BP) or the photoreducible copper(II) complex 1. In particular, BP at 1 mol% in methanol upon 365 nm irradiation with a low-pressure mercury lamp (type TLC=thin layer chromatography, 6 W) results in a fast reaction with excellent reaction yields. Complex 1 and BP 2 exhibited very similar reactivity, suggesting that the reactions involving 1 are likely to be governed by the benzophenone photoactivation processes, rather than copper(I)/(II) redox processes. Mechanistic investigations using transient absorption spectroscopy revealed that a deactivation pathway of the benzophenone triplet (3BP*) is via its reaction with the methanol solvent. We propose that the generated radicals, in particular.CH2OH, play a key role in the initiation step forming Rf.by reacting with RfI, Rf.then entering a radical chain cycle.1H NMR studies provided evidence that a substantial amount (～7% NMR yield) of the hemiacetal CH3OCH2OH is formed, i.e., the possible by-product of the reaction between.CH2OH and RfI. Finally, DFT calculations indicate that a triplet-triplet energy transfer (TTET) process from3BP* to perfluorooctyl iodide (C8F17I) is unlikely or should be rather slow under the reaction conditions, consistent with the transient absorption studies. (Figure presented.).
Self-assembled monolayers on gold generated from terminally perfluorinated alkanethiols bearing propyl vs. ethyl hydrocarbon spacers
Zenasni, Oussama,Jamison, Andrew C.,Marquez, Maria D.,Lee, T. Randall
, p. 128 - 136 (2015/03/05)
This paper examines the structural and interfacial properties of terminally perfluorinated self-assembled monolayers (FSAMs) on gold generated from the adsorption of a new series of terminally perfluorinated propanethiols F(CF2)n(CH2)3SH, where n = 8, 10, and 12. Analysis of these FSAMs by ellipsometry and X-ray photoelectron spectroscopy (XPS) confirmed the formation of the monolayer films. The contact angles of water and n-hexadecane on these FSAMs indicated a high degree of hydrophobicity and oleophobicity. Polarization modulation infrared reflection-adsorption spectroscopy (PM-IRRAS) analysis of the films revealed that the fluorinated chains are oriented largely perpendicular to the gold surface. In addition, the FSAMs formed from the new adsorbates were compared to known FSAMs derived from F(CF2)n(CH2)2SH, where n = 8, 10, and 12, to examine the influence of the number of CH2 groups in the short alkyl spacer upon the conformational order and packing structure of the films. Analysis of the XPS spectra for the normalized peak intensity of the F 1s and S 2p binding energies for both types of films suggest a slight increase in packing density for the chains having the propyl vs. the ethyl hydrocarbon spacer. This conclusion is consistent with the observed decrease in the wetting behavior of hexadecane on the FSAMs formed from the new adsorbates. However, the preponderance of the data indicates that these two series of partially fluorinated alkanethiols form films with highly similar structure/packing characteristics with no discernible "odd-even" effect between the two series.
Mesophase structure of low-wetting liquid crystalline polyacrylates with new perfluoroalkyl benzoate side groups
Martinelli, Elisa,Paoli, Francesca,Gallot, Bernard,Galli, Giancarlo
experimental part, p. 4128 - 4139 (2011/10/30)
The synthesis, thermal behavior, bulk microstructure, and wettability of new polyacrylates carrying spaced 4-perfluorohexylpropyl benzoate and 4-perfluorooctylpropyl benzoate units in the side groups were Investigated. X-ray diffraction analysis proved the formation of different smectic mesophases (SmI2, SmF2, and SmC2) and the evolution of their structures and lattice parameters with temperature. The mesophase polymorphic behavior depended on the length of the perfluorinated chain segment in the repeat unit. The electron density profiles along the smectic layer normal were drawn and provided a deeper insight into the packing of the side chains in a tilted, double layer structure. Thin polymer films were cast from solution, and their low wettability was established by measurements of contact angles with different probing liquids. We suggest that the hydrophobicity and lipophobicity of the films are enhanced by the mesophase surface structure which is mediated by the high-order, mesophase bulk structure.
Br?nsted acidic imidazolium salts containing perfluoroalkyl tails catalyzed one-pot synthesis of 1,8-dioxo-decahydroacridines in water
Shen, Wei,Wang, Li-Min,Tian, He,Tang, Jun,Yu, Jian-jun
body text, p. 522 - 527 (2009/11/30)
One-pot three-component synthesis of 1,8-dioxo-9,10-diaryl-decahydroacridines in water was efficiently realized in the presence of the Br?nsted acidic imidazolium salts containing perfluoroalkyl tails in good yields. The method provided several advantages such as low catalyst loading; recycle of the catalyst and simple work procedure.
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.
3-(Perfluoroalkyl)propanols: Valuable building blocks for fluorous chemistry
Rabai, Jozsef,Szijjarto, Csongor,Ivanko, Peter,Szabo, Denes
, p. 2581 - 2584 (2008/03/13)
2-Iodo-3-(perfluoroalkyl)propanols are obtained in excellent yields and several-hundred-gram quantities by the controlled radical addition of commercially available n-perfluoroalkyl and perfluoroisoalkyl iodides to allyl alcohol. Their consecutive reduction with hydrazine hydrate and Raney nickel catalyst in methanol afforded the corresponding 3-(perfluoroalkyl)propanols in high yields and purity. Georg Thieme Verlag Stuttgart.
