Three is company: dual intramolecular hydrogen-bond enabled carboxylic acid active in ring-opening polymerization

2016 ◽  
Vol 7 (5) ◽  
pp. 1111-1120 ◽  
Author(s):  
Jiaxi Xu ◽  
Jingjing Liu ◽  
Zhenjiang Li ◽  
Xiaopei Li ◽  
Cheng Chen ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Carboxylic Acid ◽  
Intramolecular Hydrogen Bond ◽  
Ring Opening ◽  
Active Catalyst ◽  
Ring Opening Polymerization ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Brönsted Acid ◽  
Intramolecular Hydrogen

Dual intramolecular H-bonding made weak Brønsted acid an active catalyst in cationic ring-opening polymerizations.

P-Chiral, N-phosphoryl sulfonamide Brønsted acids with an intramolecular hydrogen bond interaction that modulates organocatalysis

2019 ◽  
Vol 17 (38) ◽  
pp. 8690-8694 ◽  
Author(s):  
Minglei Yuan ◽  
Ifenna I. Mbaezue ◽  
Zhi Zhou ◽  
Filip Topic ◽  
Youla S. Tsantrizos
Keyword(s):  
Hydrogen Bond ◽  
Intramolecular Hydrogen Bond ◽  
Transfer Hydrogenation ◽  
Bronsted Acids ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Hydrogen Bond Interaction ◽  
Bond Interaction ◽  
Brönsted Acid ◽  
Intramolecular Hydrogen

An intramolecular H-bond in the Brønsted acid OttoPhosa I accelerates the reaction and increases enantioselectivity for the transfer hydrogenation of quinolines.

2,4-Dinitrobenzenesulfonic acid in an efficient Brønsted acid-catalyzed controlled/living ring-opening polymerization of ε-caprolactone

RSC Advances ◽  
2014 ◽  
Vol 4 (99) ◽  
pp. 55716-55722 ◽  
Author(s):  
Huiying Wang ◽  
Wenzhuo Wu ◽  
Zhenjiang Li ◽  
Xu Zhi ◽  
Cheng Chen ◽  
...  
Keyword(s):  
Ring Opening ◽  
Diblock Copolymers ◽  
Ring Opening Polymerization ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Acidic Catalyst ◽  
Brönsted Acid ◽  
Acid Catalyzed

2,4-Dinitrobenzenesulfonic acid as an efficient Brønsted acidic catalyst has been evaluated for the controlled/living ring-opening polymerization of ε-caprolactone end-functionalized, α,ω-dihydroxy telechelic poly(ε-caprolactone), and diblock copolymers were also synthesised successfully.

A strong cationic Brønsted acid, [H(OEt2)2][Al{OC(CF3)3}4], as an efficient initiator for the cationic ring-opening polymerization of 2-alkyl-2-oxazolines

2013 ◽  
Vol 4 (3) ◽  
pp. 495-505 ◽  
Author(s):  
Tobias Rudolph ◽  
Kristian Kempe ◽  
Sarah Crotty ◽  
Renzo M. Paulus ◽  
Ulrich S. Schubert ◽  
...  
Keyword(s):  
Ring Opening ◽  
Ring Opening Polymerization ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Brönsted Acid ◽  
Cationic Ring Opening Polymerization

scholarly journals Solventless Sol-Gel Chemistry Through Ring-Opening Polymerization of Bridged Disilaoxacyclopentanes

2000 ◽  
Vol 628 ◽  
Author(s):  
Kamyar Rahimian ◽  
Douglas A. Loy
Keyword(s):  
Ring Opening ◽  
Sol Gel ◽  
Ring Opening Polymerization ◽  
Inorganic Materials ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Organic Base ◽  
Triflic Acid ◽  
Brönsted Acid

Ring-opening polymerization (ROP) of disilaoxacyclopentanes has proven to be an excellent approach to sol-gel type hybrid orgainc-inorganic materials [1]. These materials have shown promise as precursors for encapsulation and microelectronics applications (Figure 1). The polymers are highly crosslinked and are structurally similar to traditional sol-gels, but unlike typical sol-gels they are prepared by an organic base or Bronsted acid (formic or triflic acid), without the use of solvents and water, they have low VOC's and show little shrinkage during processing.

(1′R,3S)-2-Oxo-1-(1′-phenylethyl)piperidine-3-carboxylic acid: a case of a very strong intramolecular hydrogen bond

2004 ◽  
Vol 60 (11) ◽  
pp. o2110-o2112
Author(s):  
Ana-María Lumbreras-García ◽  
Alberto Galindo-Guzmán ◽  
Dino Gnecco ◽  
Joel-Luis Terán ◽  
Sylvain Bernès
Keyword(s):  
Hydrogen Bond ◽  
Carboxylic Acid ◽  
Intramolecular Hydrogen Bond ◽  
Intramolecular Hydrogen ◽  
Strong Intramolecular Hydrogen Bond

scholarly journals Alkyl Ethers as Traceless Hydride Donors in Brønsted Acid Catalyzed Intramolecular Hydrogen Atom Transfer

2018 ◽  
Vol 57 (21) ◽  
pp. 6181-6185 ◽  
Author(s):  
Dhika Aditya Gandamana ◽  
Bin Wang ◽  
Ciputra Tejo ◽  
Benoit Bolte ◽  
Fabien Gagosz ◽  
...  
Keyword(s):  
Hydrogen Atom ◽  
Hydrogen Atom Transfer ◽  
Atom Transfer ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Brönsted Acid ◽  
Alkyl Ethers ◽  
Acid Catalyzed ◽  
Intramolecular Hydrogen

scholarly journals Zirconium (IV) Acetylacetonate: Ring-Opening Initiator Mediating One-Step Synthesis of Biodegradable Polyacids

2019 ◽  
Vol 2019 ◽  
pp. 1-10 ◽  
Author(s):  
Piotr Dobrzyński ◽  
Małgorzata Pastusiak ◽  
Joanna Jaworska ◽  
Bożena Kaczmarczyk ◽  
Michał Kwiecień ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Acid Derivative ◽  
Ring Opening ◽  
Active Catalyst ◽  
Ring Opening Polymerization ◽  
Cyclic Carbonate ◽  
Trimethylene Carbonate ◽  
Step Method ◽  
Polymerization Mechanism ◽  
One Step

Biodegradable polyacid is obtained in one-step ring-opening polymerization (ROP) of carboxylic-acid-functionalized six-membered cyclic carbonate mediated with zirconium (IV) acetylacetonate. Exemplary copolymers with L,L-lactide are described as well. Moreover, zirconium (IV) acetylacetonate is found to be active catalyst of trimethylene carbonate (TMC) ROP in presence of carboxylic acid yielding PTMC end-capped with the acid derivative. Polymerization mechanism is hypothesized demonstrating possibilities of the method in work-saving polycation synthesis and one-step method of conjugate synthesis of well-known biocompatible polyesters and polycarbonates.

Ring-Opening Hydroarylation of Monosubstituted Cyclopropanes Enabled by Hexafluoroisopropanol

2018 ◽  
Author(s):  
Edward Richmond ◽  
Jing Yi ◽  
Vuk D. Vuković ◽  
Fatima Sajadi ◽  
Christopher Rowley ◽  
...  
Keyword(s):  
Dft Calculations ◽  
Ring Opening ◽  
Bond Formation ◽  
Conjugate Addition ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Broad Scope ◽  
Brönsted Acid ◽  
Donor Acceptor ◽  
Addition Pathway

<div><p>Ring-opening hydroarylation of cyclopropanes is typically limited to substrates bearing a donor-acceptor motif. Here, the transformation is achieved for monosubstituted cyclopropanes by using catalytic Brønsted acid in hexafluoroisopropanol (HFIP) solvent, constituting a rare example where such cyclopropanes engage in intermolecular C–C bond formation. Branched products are obtained when electron-rich arylcyclopropanes react with a broad scope of arene nucleophiles in accord with a simple S<sub>N</sub>1-type ring-opening mechanism. In constrast, linear products are obtained when cyclopropylketones react with electron-rich arene nucleophiles. In the latter case, mechanistic experiments and DFT-calculations support a homo-conjugate addition pathway.</p></div>

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