Dynamic Covalent Chemistry of the Nicholas Ether-Exchange Reaction

2009 ◽  
Vol 11 (6) ◽  
pp. 1313-1316 ◽  
Author(s):  
Nobuhiro Kihara ◽  
Kazuyuki Kidoba
Keyword(s):  
Exchange Reaction ◽  
Dynamic Covalent Chemistry

Trithioorthoester Exchange and Metathesis: New Tools for Dynamic Covalent Chemistry

Synlett ◽  
2019 ◽  
Vol 30 (17) ◽  
pp. 1988-1994
Author(s):  
Michael Bothe ◽  
A. Gastón Orrillo ◽  
Ricardo L. E. Furlan ◽  
Max von Delius
Keyword(s):  
Porous Materials ◽  
Exchange Reaction ◽  
Lewis Acids ◽  
High Stability ◽  
Distinct Advantage ◽  
Bronsted Acids ◽  
Residual Moisture ◽  
Dynamic Covalent Chemistry ◽  
Systems Chemistry ◽  
Acid Catalyzed

To expand the toolbox of dynamic covalent and systems chemistry, we investigated the acid-catalyzed exchange reaction of trithioorthoesters with thiols. We found that trithioorthoester exchange occurs readily in various solvents in the presence of stoichiometric amounts of strong Brønsted acids or catalytic amounts of certain Lewis acids. The scope of the exchange reaction was explored with various substrates, and conditions were identified that permit clean metathesis reactions between two different trithioorthoesters. One distinct advantage of S,S,S-orthoester exchange over O,O,O-orthoester exchange is that the exchange reaction can kinetically outcompete hydrolysis, thereby making the process less sensitive to residual moisture. We expect that the relatively high stability of the products might be beneficial in future supramolecular receptors or porous materials.

Pyridyl disulfide-based thiol–disulfide exchange reaction: shaping the design of redox-responsive polymeric materials

2020 ◽  
Vol 11 (48) ◽  
pp. 7603-7624
Author(s):  
Ismail Altinbasak ◽  
Mehmet Arslan ◽  
Rana Sanyal ◽  
Amitav Sanyal
Keyword(s):  
Exchange Reaction ◽  
Functional Materials ◽  
Polymeric Materials ◽  
Disulfide Exchange ◽  
Redox Responsive ◽  
Synthetic Approaches

This review provides an overview of synthetic approaches utilized to incorporate the thiol-reactive pyridyl-disulfide motif into various polymeric materials, and briefly highlights its utilization to obtain functional materials.

Formation and Trapping of the Thermodynamically Unfavoured Inverted-Hemicucurbit[6]uril

2019 ◽  
Author(s):  
Elena Prigorchenko ◽  
Sandra Kaabel ◽  
Triin Narva ◽  
Anastassia Baškir ◽  
Maria Fomitšenko ◽  
...  
Keyword(s):  
Complex Formation ◽  
Combinatorial Chemistry ◽  
Trifluoroacetic Acid ◽  
Chloride Anion ◽  
Binding Affinities ◽  
Dynamic Covalent Chemistry ◽  
Reaction Selectivity ◽  
Low Concentration ◽  
Dynamic Combinatorial Chemistry ◽  
First Time

Amplification of a thermodynamically unfavoured macrocyclic product through the directed shift of the equilibrium between dynamic covalent chemistry library members is difficult to achieve. We show for the first time that during condensation of formaldehyde and <i>cis</i>-<i>N,N'</i>-cyclohexa-1,2-diylurea formation of <i>inverted-cis</i>-cyclohexanohemicucurbit[6]uril (<i>i-cis</i>-cycHC[6]) can be induced at the expense of thermodynamically favoured <i>cis</i>-cyclohexanohemicucurbit[6]uril (<i>cis</i>-cycHC[6]). The formation of <i>i-cis-</i>cycHC[6] is enhanced in low concentration of the templating chloride anion and suppressed in excess of this template. We found that reaction selectivity is governed by the solution-based template-aided dynamic combinatorial chemistry and continuous removal of the formed cycHC[6] macrocycles from the equilibrating solution by precipitation. Notably, the <i>i-cis</i>-cycHC[6] was isolated with 33% yield. Different binding affinities of three diastereomeric <i>i-cis</i>-, <i>cis</i>-cycHC[6] and their chiral isomer (<i>R,R</i>)-cycHC[6] for trifluoroacetic acid demonstrate the influence of macrocycle geometry on complex formation.

Photoassisted Production of O2-• and H2 in Aqueous Medium Stimulated by Polythiophene in ZSM-5 Zeolite Channels

1999 ◽  
Vol 64 (1) ◽  
pp. 149-156 ◽  
Author(s):  
Gabriel Čík ◽  
František Šeršeň ◽  
Alena Bumbálová
Keyword(s):  
Reactive Oxygen Species ◽  
Ion Exchange ◽  
Visible Light ◽  
Aqueous Medium ◽  
Exchange Reaction ◽  
Epr Spectroscopy ◽  
Reactive Oxygen ◽  
Oxygen Species ◽  
Water Reduction ◽  
Ion Exchange Reaction

The formation of reactive oxygen species due to irradiation by a visible light of the polythiophene deposited in ZSM-5 zeolite channels in aqueous medium has been studied. Polymerization of thiophene was carried out in zeolite channels after the ion-exchange reaction of Na+ for Fe3+. By means of EPR spectroscopy, the temporarily generated 1O2 in irradiated aqueous medium was proved. The formation of O2-• was confirmed by the reduction of Fe3+-cytochrome c. Irradiation led to the water reduction to hydrogen.

scholarly journals Inhibition of Spleen Diphosphopyridine Nucleotidase by Nicotinamide, An Exchange Reaction

1953 ◽  
Vol 200 (1) ◽  
pp. 197-212 ◽  
Author(s):  
Leonard J. Zatman ◽  
Nathan O. Kaplan ◽  
Sidney P. Colowick
Keyword(s):  
Exchange Reaction

scholarly journals Ni-Catalyzed Aryl Sulfide Synthesis through an Aryl Exchange Reaction

2021 ◽  
Author(s):  
Ryota Isshiki ◽  
Miki B. Kurosawa ◽  
Kei Muto ◽  
Junichiro Yamaguchi
Keyword(s):  
Exchange Reaction ◽  
Aryl Sulfide

scholarly journals Spontaneous macrocyclization through multiple dynamic cyclic aminal formation

2021 ◽  
Author(s):  
Daniel Carbajo ◽  
Antonio Jesús Ruiz-Sánchez ◽  
Francisco Nájera Albendín ◽  
Ezequiel Perez-Inestrosa ◽  
Ignacio Alfonso
Keyword(s):  
Dynamic Covalent Chemistry

The use of aminals in dynamic covalent chemistry is slightly underexplored, probably due to their inherent instability. Here we report the spontaneous [2+2] macrocyclization of tetrakis(aminals). Their unexpected stability and...

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