Cascade Assembly of 4,5,6,7-Tetrahydroindole from Cyclohexanone Oxime and Acetylene in the KOH/DMSO Superbase Medium: A Quantum Chemical Study

Bobkov, Alexander S.; Vitkovskaya, N. M.; Трофимов, Б. А.

doi:10.1021/acs.joc.0c00353

Cited by 10 publications

(3 citation statements)

References 31 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…CCPz Fabrication: Freestanding polymer layers and TFC polymeric membranes were formed by interfacial polymerization of 1) a 10 w/v% solution of the corresponding biphenols in DMSO containing KOH (super base); [55] molar ratio of biphenol:KOH of 0.5, that is, stoichiometric with respect to phenol groups, and 0.75, that is, substoichiometric with respect to phenol groups and 2) a 3.5 w/v% HCCP solution in cyclohexane.…”

Section: Methodsmentioning

confidence: 99%

Thin‐Film Composite Cyclomatrix Poly(Phenoxy)Phosphazenes Membranes for Hot Hydrogen Separation

Radmanesh

Sudhölter

Tena

et al. 2022

Adv Materials Inter

View full text Add to dashboard Cite

An interfacial polymerization process is introduced for the fabrication of thermally stable cyclomatrix poly(phenoxy)phosphazenes thin‐film composite membranes that can sieve hydrogen from hot gas mixtures. By replacing the conventionally used aqueous phase with dimethyl sulfoxide/potassium hydroxide, a variety of biphenol molecules are deprotonated to aryloxide anions that react with hexachlorocyclotriphosphazene dissolved in cyclohexane to form a thin film of a highly cross‐linked polymer film. The film membranes have persistent permselectivities for hydrogen over nitrogen (16–27) and methane (14–30) while maintaining hydrogen permeances in the order of (10−8–10−7 mol m−2s−1Pa−1) at temperatures as high as 260 °C and do not lose their performance after exposure to 450 °C. The unprecedented thermal stability of these polymer membranes opens the potential for industrial membrane gas separations at elevated temperatures.

show abstract

Section: Methodsmentioning

confidence: 99%

Thin‐Film Composite Cyclomatrix Poly(Phenoxy)Phosphazenes Membranes for Hot Hydrogen Separation

Radmanesh

Sudhölter

Tena

et al. 2022

Adv Materials Inter

View full text Add to dashboard Cite

show abstract

“…Material Fabrication. Free-standing polymeric layers and thin-film composite membranes were formed by interfacial polymerization of a 10 w/v % solution of the AHCs in super base 26 DMSO and KOH, with a 3.5 w/v % HCCP solution in cyclohexane. The molar ratio of monomer hydroxyl groups to KOH is indicated by x and was kept at 4:1, 3.5:1, and 2.2:1 in DMSO unless mentioned otherwise.…”

Section: Methodsmentioning

confidence: 99%

Nonaqueous Interfacial Polymerization-Derived Polyphosphazene Films for Sieving or Blocking Hydrogen Gas

Radmanesh

Tena

Sudhölter

et al. 2023

ACS Appl. Polym. Mater.

View full text Add to dashboard Cite

A series of cyclomatrix polyphosphazene films have been prepared by nonaqueous interfacial polymerization (IP) of small aromatic hydroxyl compounds in a potassium hydroxide dimethylsulfoxide solution and hexachlorocyclotriphosphazene in cyclohexane on top of ceramic supports. Via the amount of dissolved potassium hydroxide, the extent of deprotonation of the aromatic hydroxyl compounds can be changed, in turn affecting the molecular structure and permselective properties of the thin polymer networks ranging from hydrogen/oxygen barriers to membranes with persisting hydrogen permselectivities at high temperatures. Barrier films are obtained with a high potassium hydroxide concentration, revealing permeabilities as low as 9.4 × 10 −17 cm 3 cm cm −2 s −1 Pa −1 for hydrogen and 1.1 × 10 −16 cm 3 cm cm −2 s −1 Pa −1 for oxygen. For films obtained with a lower concentration of potassium hydroxide, single gas permeation experiments reveal a molecular sieving behavior, with a hydrogen permeance of around 10 −8 mol m −2 s −1 Pa −1 and permselectivities of H 2 /N 2 (52.8), H 2 /CH 4 (100), and H 2 /CO 2 (10.1) at 200 °C.

show abstract

“…As it can be seen from the Table 1 , Trofimov et al . studied this reaction more deeply and much more widely using various superbasic systems, various suppliers of two-carbon fragments (not only acetylene (Table 1 , entries 1, 4–7), 49 51 , 52` b c d e and also chloro- and bromoethenes (entry 2), 49 dichloro- and dibromoethanes (entries 3 and 8–10), 49 52f g instead of oximes, corresponding ketones and hydroxylamine hydrochloride (entries 6–10), 49 52f g varying the reaction conditions.…”

Section: Intermolecular Reactions Leading To Tetrahydroindolesmentioning

confidence: 99%

Recent Advances in the Synthesis of Indoles with Partially Hydrogenated Benzene Ring (Tetrahydroindoles)

Mamedov,

Zhukova

2023

Synthesis

View full text Add to dashboard Cite

In this review, a fragmentary analysis of 4,5,6,7-tetrahydroindoles was performed and, on its basis, the existing methods of their synthesis published over the past 15 years have been summarized, and analyzed, as well as, if necessary, an analysis of earlier works is carried out. The proposed reaction mechanism is considered, as well as factors that significantly influence the course of the process. Among such factors: temperature, type and content of the catalyst, promoting additives, method of the process, etc. Particular attention is paid to fundamentally new methods that make it possible to synthesize various derivatives of the mentioned heterocyclic systems from available and cheap reagents, and in some cases under environmentally benign conditions.1 Introduction2 Intramolecular Reactions Leading To Tetrahydroindoles2.1 Ring Closure Reactions with N–C2 Bond Formation (a)2.2 Ring Closure Reactions with C2–C3 Bond Formation (b)2.3 Ring Closure Reactions with C3–C3a Bond Formation (c)2.4 Ring Closure Reactions with C7a–N Bond Formation (e)2.5 Ring Closure Reactions with C4–C5 Bond Formation (g)2.6 Ring Closure Reactions with C3a–C4 Bond Formation (h)3 Intermolecular Reactions Leading To Tetrahydroindoles3.1 Ring Closure Reactions with N–C2 + C3–C3a Bond Formation (ac)3.2 Ring Closure reactions with N–C2 + C7a–N Bond Formation (ae)3.3 Ring Closure reactions with C3–C3a + C7a–N Bond formation (ce)3.4 Ring Closure Reactions with N–C2, C3–C3a, and C7a–N Bond Formation (ace)4 Recovery Processes (Hydrogenation) of Indoles and Oxidation of Perhydroindoles in the Synthesis of 4,5,6,7-Tetrahydroindoles5 Conclusion

show abstract

Cascade Assembly of 4,5,6,7-Tetrahydroindole from Cyclohexanone Oxime and Acetylene in the KOH/DMSO Superbase Medium: A Quantum Chemical Study

Cited by 10 publications

References 31 publications

Thin‐Film Composite Cyclomatrix Poly(Phenoxy)Phosphazenes Membranes for Hot Hydrogen Separation

Thin‐Film Composite Cyclomatrix Poly(Phenoxy)Phosphazenes Membranes for Hot Hydrogen Separation

Nonaqueous Interfacial Polymerization-Derived Polyphosphazene Films for Sieving or Blocking Hydrogen Gas

Recent Advances in the Synthesis of Indoles with Partially Hydrogenated Benzene Ring (Tetrahydroindoles)

Contact Info

Product

Resources

About