α,ω-Difunctional Perfluorinated Spacer Arms for Polymeric Material Derivatization

Mougenot, Patrick; Mertens, P.; Nguyen, Minh Tho; Touillaux, Roland; Marchand‐Brynaert, Jacqueline

doi:10.1021/jo951248n

Cited by 9 publications

(4 citation statements)

References 45 publications

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“…Under the optimized conditions, the reactions performed well with linear, branched, and aromatic fluorinated alkoxides featuring 3–17 fluorine atoms to afford the desired products 2a–g in 55–90% yield. Even a diol was effective in order to get a symmetrical difunctional compound with a polyfluorinated spacer arm 2h as the potential structure for the construction of new materials . All synthesized molecules were new and were fully characterized (see the Supporting Information).…”

Section: Resultsmentioning

confidence: 99%

Amphiphilic Polyfluorinated Amino Ethers from Cyclic Sulfamidates

Marie

Cahard

2022

J. Org. Chem.

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Section: Resultsmentioning

confidence: 99%

Amphiphilic Polyfluorinated Amino Ethers from Cyclic Sulfamidates

Marie

Cahard

2022

J. Org. Chem.

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“…The methyl 3,5,6-tri- O -benzyl- d -α-β-glucofuranoside ( 4 ) prepared according to the synthesis reported by Lee et al . has been successively coupled with 3-bromo- N -(1- tert -butoxycarbonyl)propylamine, N -bromooctylphthalimide, and commercially available 1,2-bis(2-chlorethoxy)ethane in DMF at room temperature in the presence of sodium hydride. The corresponding N -protected aminopropyl and aminooctyl sugars 5a and 5b were obtained after 14 h with respective yields of 65% and 71%.…”

Section: Resultsmentioning

confidence: 99%

Versatile Routes to C-2- and C-6-Functionalized Glucose Derivatives of Iminodiacetic Acid

2002

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A series of novel d-glucose derivatives, functionalized at the C-2 or the C-6 position with an iminodiacetic acid moiety for transition-metal complexation, has been prepared. The sugar and the metal-chelating parts are separated by either propyl or octyl chains and were introduced by the reaction of bromoalkylamine. Either N-1-Boc-3-bromopropylamine (17) or N-(8-bromooctyl)phthalimide (19) reacted with methyl 3,5,6-tri-O-benzyl-α-β-d-glucofuranoside (4) (C-2 position) and 1,2:3,5-(O-methylene)-α-d-glucose (11) (C-6 position), respectively, in the presence of sodium hydride in DMF at room temperature, affording the desired intermediates. For aminopropyl derivatives, yields varied between 57% and 65%, and for aminooctyl derivatives, yields varied between 40% and 71%. After deprotection of the amine functionality, the metal chelate was built up by dialkylation (6a − c and 13a,b) with methyl bromoacetate in the presence of triethylamine under reflux in THF. Yields varied between 56% and 69% for the glucose modified at the C-2 position and between 58% and 62% for the one modified at the C-6 position. All compounds were characterized by 1H or 13C NMR or both, IR, and mass spectroscopy. Final products were isolated as a mixture of α and β anomers.

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“…Since the commonly used perfluoroalkyl iodides are monofunctional reagents, they allow the introduction of perfluorinated units only into terminal positions. 3,4 Consequently, the development of effective synthesis of X(CF 2 ) n Y type reagents could provide larger structural versatility for the synthesis of fluorophilic 3 and multiblock compounds, including liquid crystalline structures, 5 biomaterials, 6 and self-assembled polymeric systems. 7 In this Letter we describe a convenient method for the synthesis of ω-functionalized perfluoroalkyl iodides, useful building blocks of compounds containing the -( bacic acid 8 and used for the construction of a reverse F-amphiphile.…”

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confidence: 99%

“…Fluorous methods have opened wide perspectives also in combinatorial synthesis 2c and produced a firm market for designed 3 fluorous reagents and labels. Since the commonly used perfluoroalkyl iodides are monofunctional reagents, they allow the introduction of perfluorinated units only into terminal positions. , Consequently, the development of effective synthesis of X(CF 2 ) n Y type reagents could provide larger structural versatility for the synthesis of fluorophilic 3 and multiblock compounds, including liquid crystalline structures, biomaterials, and self-assembled polymeric systems …”

mentioning

confidence: 99%

A Novel Strategy for the Synthesis of ω-Functionalized Perfluoroalkyl Iodides

et al. 2001

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[reaction: see text] The applicability of telomeric alcohols, H(CF(2)CF(2))(n)()CH(2)OH, for the synthesis of omega-functionalized F-alkylating reagents, I(CF(2)CF(2))(n-1)CH(2)OAc (6, n = 5), is demonstrated. The key steps of this optimized method are the "activation" of the HCF(2)- terminus in a lithiation process yielding olefin 2 [(Z+E)-BuCF=CF(CF(2)CF(2))(4)CH(2)OH, 86%] and a successive ozonation reaction in trifluoroethanol media affording ester 3b [CF(3)CH(2)O(2)C(CF(2)CF(2))(4)CH(2)OH, 93%]. Highly stereospecific ozone cleavage of the (E)-2 isomer was observed in methanol due to the competitive oxidation of the solvent.

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α,ω-Difunctional Perfluorinated Spacer Arms for Polymeric Material Derivatization

Cited by 9 publications

References 45 publications

Amphiphilic Polyfluorinated Amino Ethers from Cyclic Sulfamidates

Amphiphilic Polyfluorinated Amino Ethers from Cyclic Sulfamidates

Versatile Routes to C-2- and C-6-Functionalized Glucose Derivatives of Iminodiacetic Acid

A Novel Strategy for the Synthesis of ω-Functionalized Perfluoroalkyl Iodides

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