Facile Synthesis of Hydroxy-Substituted Thiacrown Ethers via Nucleophilic Ring Opening of Epoxides

Synthesis ◽  
2019 ◽  
Vol 51 (10) ◽  
pp. 2214-2220 ◽  
Author(s):  
Monika Stefaniak ◽  
Jarosław Romański
Keyword(s):  
Click Chemistry ◽  
Ring Opening ◽  
Facile Synthesis ◽  
Step Procedure ◽  
Ring Opening Of Epoxides ◽  
One Step ◽  
Thiacrown Ethers ◽  
Hydroxy Groups ◽  
First Time ◽  
Nucleophilic Ring Opening

The title thiacrown ethers were prepared in a one-step procedure to give a series of unique macrocycles possessing two unsubstituted hydroxy groups that can be easily functionalized. In addition, epoxides and macrocycles derived from Cookson’s birdcage diketone, were prepared. The nucleophilic ring opening of epoxides synthesis can be classified in the frame of click chemistry. Surprisingly, some of the prepared allyl substituted polyglycols as well as bis-epoxides, especially sulfur analogues, were prepared for the first time.

scholarly journals Electrochromic Performance and Capacitor Performance of α-MoO3 Nanorods Fabricated by a One-Step Procedure

Coatings ◽  
2021 ◽  
Vol 11 (7) ◽  
pp. 783
Author(s):  
Ying Duan ◽  
Chen Wang ◽  
Jian Hao ◽  
Yang Jiao ◽  
Yanchao Xu ◽  
...  
Keyword(s):  
Growth Parameters ◽  
Average Diameter ◽  
Fast Response ◽  
Cycle Stability ◽  
Electrochromic Devices ◽  
Step Procedure ◽  
One Step ◽  
Supercapacitor Performance ◽  
First Time ◽  
Prepared Nanorods

In this paper, we propose for the first time the synthesis of α-MoO3 nanorods in a one-step procedure at mild temperatures. By changing the growth parameters, the microstructure and controllable morphology of the resulting products can be customized. The average diameter of the as-prepared nanorods is about 200 nm. The electrochromic and capacitance properties of the synthesized products were studied. The results show that the electrochromic properties of α-MoO3 nanorods at 550 nm have 67% high transmission contrast, good cycle stability and fast response time. The MoO3 nanorods also exhibit a stable supercapacitor performance with 98.5% capacitance retention after 10,000 cycles. Although current density varies sequentially, the nanostructure always exhibits a stable capacitor to maintain 100%. These results indicate the as-prepared MoO3 nanorods may be good candidates for applications in electrochromic devices and supercapacitors.

Nucleophilic ring-opening of epoxides: trends in β-substituted alcohols synthesis

2018 ◽  
Vol 15 (9) ◽  
pp. 2033-2081 ◽  
Author(s):  
Mehdi Fallah-Mehrjardi ◽  
Ali Reza Kiasat ◽  
Khodabakhsh Niknam
Keyword(s):  
Ring Opening ◽  
Ring Opening Of Epoxides ◽  
Nucleophilic Ring Opening

Catalyst Free, Nitromethane Assisted Facile Ring Opening of Epoxide with Less Reactive Aromatic Amines

2020 ◽  
Author(s):  
Sumit Kumar ◽  
Meenakshi Bansal ◽  
Charu Upadhyay ◽  
Maria Grishina ◽  
Vladimir Potemkin ◽  
...  
Keyword(s):  
Aromatic Amines ◽  
Ring Opening ◽  
Spectroscopic Studies ◽  
Bioactive Scaffolds ◽  
Chemistry Research ◽  
Ring Opening Reactions ◽  
Ring Opening Of Epoxide ◽  
Sterically Hindered ◽  
First Time ◽  
Nucleophilic Ring Opening

<p>Nucleophilic ring opening reactions of epoxides with aromatic amines are in the forefront of the synthetic organic chemistry research to build new bioactive scaffolds. Here, a convenient, green and highly efficient regioselective ring opening of sterically hindered (2R,3S)-3-(<i>N</i>-Boc-amino)-1-oxirane-4-phenylbutane with various poorly reactive aromatic amines are accomplished under microwave irradiation in nitromethane. All the reactions effectively implemented for various aromatic amines involves reuse of nitromethane that supports its dual role as a solvent and catalyst. The corresponding new β-alcohol analogs of hydroxyethylamine (HEA) are isolated in 41-98% yields. The reactions proceed under mild conditions for a broad range of less reactive and sterically hindered aromatic amines. Proton NMR and UV-visible spectroscopic studies suggest that the nucleophilicity of amines is influenced by nitromethane, which is substantiated by the extensive computational studies. Overall, this methodology elucidates the first time use of nitromethane as a solvent for the ring opening reactions under microwave conditions involving equimolar ratio of epoxide and aromatic amine without any catalyst, facile ring opening of complex epoxide by less reactive aromatic amines, low reaction time, less energy consumption, recycling of the solvent and simple workup procedures.</p>

scholarly journals Asymmetric Ring-Opening of Epoxides Catalyzed by Metal–Salen Complexes

Catalysts ◽  
2020 ◽  
Vol 10 (6) ◽  
pp. 705
Author(s):  
Anna Lidskog ◽  
Yutang Li ◽  
Kenneth Wärnmark
Keyword(s):  
Functional Groups ◽  
Organic Synthesis ◽  
Ring Opening ◽  
Kinetic Resolution ◽  
Catalytic Systems ◽  
Salen Complexes ◽  
Epoxide Opening ◽  
Ring Opening Of Epoxides ◽  
One Step ◽  
Asymmetric Ring Opening

The asymmetric ring-opening of epoxides is an important reaction in organic synthesis, since it allows for the enantioselective installation of two vicinal functional groups with specific stereochemistry within one step from a highly available starting material. An effective class of catalysts for the asymmetric ring-opening of epoxides is metal–salen complexes. This review summarizes the development of metal–salen catalyzed enantioselective desymmetrization of meso-epoxides and kinetic resolution of epoxides with various nucleophiles, including the design and application of both homogeneous- and heterogeneous epoxide-opening catalysts as well as multi-metallic covalent and supramolecular catalytic systems.

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