Perfluoroalkyl bile esters: a new class of efficient gelators of organic and aqueous–organic media

Banerjee, Supratim; Vidya, V.; Savyasachi, Aramballi J.; Maitra, Uday

doi:10.1039/c1jm11912e

Cited by 24 publications

(26 citation statements)

References 56 publications

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“…The precipitate was filtered off; the solvent was evaporated on a rotor, obtaining the desired tosylates. The melting points were identical to published data: 1 (52-53 [19]), 2 (13-15 [20]), 3 (34-35 [21]), and 4 (43-44 • C [20]). The yields for 1-4 are equal to 80, 87, 95, and 95%, respectively.…”

Section: Synthesis Of Tosylates 1-4supporting

confidence: 85%

Molecular Structures Polymorphism the Role of F…F Interactions in Crystal Packing of Fluorinated Tosylates

et al. 2019

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The peculiarities of interatomic interactions formed by fluorine atoms were studied in four tosylate derivatives p-CH3C6H4OSO2CH2CF2CF3 and p-CH3C6H4OSO2CH2(CF2)nCHF2 (n = 1, 5, 7) using X-ray diffraction and quantum chemical calculations. Compounds p-CH3C6H4OSO2CH2(CF2)nCHF2 (n = 1, 5) were crystallized in several polymorph modifications. Analysis of intermolecular bonding was carried out using QTAIM approach and energy partitioning. All compounds are characterized by crystal packing of similar type and the contribution of intermolecular interactions formed by fluorine atoms to lattice energy is raised along with the increase of their amount. The energy of intra- and intermolecular F…F interactions is varied in range 0.5–13.0 kJ/mol. Total contribution of F…F interactions to lattice energy does not exceed 40%. Crystal structures of studied compounds are stabilized mainly by C-H…O and C-H…F weak hydrogen bonds. The analysis of intermolecular interactions and lattice energies in polymorphs of p-CH3C6H4OSO2CH2(CF2)nCHF2 (n = 1, 5) has shown that most stabilized are characterized by the least contribution of F…F interactions.

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Section: Synthesis Of Tosylates 1-4supporting

confidence: 85%

Molecular Structures Polymorphism the Role of F…F Interactions in Crystal Packing of Fluorinated Tosylates

et al. 2019

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“…Finally, unprotected cholic acid NHP ester could be coupled in high yield, even with three unprotected alcohols. 25 …”

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confidence: 99%

Decarboxylative Cross-Electrophile Coupling of N-Hydroxyphthalimide Esters with Aryl Iodides

et al. 2016

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A new method for the decarboxylative coupling of alkyl N-hydroxyphthalimide esters (NHP esters) with aryl iodides is presented. In contrast to previous studies that form alkyl radicals from carboxylic acid derivatives, no photocatalyst, light, or arylmetal reagent is needed, only nickel and a reducing agent (Zn). Methyl, primary, and secondary alkyl groups can all be coupled in good yield (77% ave yield). One coupling with an acid chloride is also presented. Stoichiometric reactions of (dtbbpy)Ni(2-tolyl)I with an NHP ester show for the first time that arylnickel(II) complexes can directly react with NHP esters to form alkylated arenes.

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“…Classical transformation of an alcoholic hydroxyl group into a better leaving group, such as tosylate, mesylate, or incorporation of iodide instead a hydroxyl group, provide the opportunity to obtain the desired products. 14,[26][27][28][29][30][31][32][33][34][35][36] In our recent studies, we focused on the long chain compounds which possess a fluorinated alkyl chain and a different -CH2-linkers attached directly to the azido group. Although the preparation of azides is very well documented, there are no much precedences to synthesize fluorinated analogues.…”

Section: Resultsmentioning

confidence: 99%

“…A procedure for preparation of fluoroalkyl tosylates is described by Zhu et al, 14 and we have used an analogous procedure to prepare fluoroalkyl mesylates (Table 1). 24,29,32,34,36,39 other bases were used such as sodium or potassium hydroxide 2a, 24,41 3a, 30,35 5a, 42,43 pyridine 1a, 44 diisopropylamine 4b, 39 DABCO 1a. 45 For compound 1b different conditions also used SbCl5.…”

Section: Resultsmentioning

confidence: 99%

Fluorinated organic azides – their preparation and synthetic application

Tomaszewska¹,

Koroniak-Szejn²,

Koroniak³

2016

Arkivoc

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Alkyl azides are widely used in many reactions. Although synthesis of such species is relatively well documented, fluorinated azides, especially with large perfluorinated or highly fluorinated groups, are sometimes tricky to make. The presence of fluorine in reacting molecules, sometimes causes significant changes in the reactivity of reacting species. In this paper we give a short overview of re-examination of currently available methods of synthesis of selected azides with highly fluorinated groups.

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Perfluoroalkyl bile esters: a new class of efficient gelators of organic and aqueous–organic media

Cited by 24 publications

References 56 publications

Molecular Structures Polymorphism the Role of F…F Interactions in Crystal Packing of Fluorinated Tosylates

Molecular Structures Polymorphism the Role of F…F Interactions in Crystal Packing of Fluorinated Tosylates

Decarboxylative Cross-Electrophile Coupling of N-Hydroxyphthalimide Esters with Aryl Iodides

Fluorinated organic azides – their preparation and synthetic application

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