Studies of the Model Compounds of Cyclopolymers. An NMR Spectroscopic Study of cis and trans Isomers of 2, 5-Dimethoxytetrahydrofuran

doi:10.1246/BCSJ.40.130

Paper

Studies of the Model Compounds of Cyclopolymers. An NMR Spectroscopic Study of cis and trans Isomers of 2, 5-Dimethoxytetrahydrofuran

Published 1967 · Yuzo Aito, T. Matsuo, C. Aso

Bulletin of the Chemical Society of Japan

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Abstract

The configurational isomers of 2, 5-dimethoxytetrahydrofuran were synthesized as model compounds of the cyclopolymer of succinaldehyde. The NMR spectra of the isomers were then studied in carbon tetrachloride and in benzene. From the behavior of the methyl and methylene protons of the isomers in chemical shifts and in the formation of a “loose-complex” with benzene, it was concluded that the isomer with the lower boiling point had a trans configuration and that the isomer with the higher boiling point had a cis configuration. The NMR spectrum of 2, 5-dimethoxy-2, 5-dihydrofuran was similarly investigated in order to compare it with that of 2, 5-dimethoxytetrahydrofuran. The spectrum was rather simple; each signal was assigned to the cis or to the trans configurational isomer.

Study Snapshot

The NMR spectra of 2, 5-dimethoxytetrahydrofuran show that the lower boiling point isomer has a trans configuration and the higher boiling point isomer has a cis configuration, indicating that the cyclopolymer of succinaldehyde has two configuration

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Studies of the Model Compounds of Cyclopolymers. An NMR Spectroscopic Study of cis and trans Isomers of 2, 5-Dimethoxytetrahydrofuran

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References

Studies on the polymerization of bifunctional monomers. VI. Cyclopolymerization of succinaldehyde

Cyclopolymerization of succinaldehyde occurs, with the polyether mainly composed of tetrahydrofuran rings as recurring units, based on solubility, fusibility, and low aldehyde content.

Far‐Infrared Spectrum of Tetrahydrofuran: Spectroscopic Evidence for Pseudorotation

Tetrahydrofuran exhibits pseudorotation in the infrared spectrum, with a complex spectrum interpreted in terms of the theory of puckered ring pseudorotation.

TEMPERATURE AND SOLVENT EFFECTS ON THE PROTON MAGNETIC RESONANCE SPECTRUM OF BIS(2,2-DICHLOROCYCLOPROPYL) ETHER

The proton magnetic resonance spectrum of bis(2,2-dichlorocyclopropyl) ether shows complex formation with benzene, with the most abundant isomer having the highest heat of formation and entropy of formation.

Citations

Synthesis of meso- and (±)-2,2′-bis(carboxymethoxy)oxydiacetic acid via cis- and trans-2,5-(diallyloxy)-2,5-dihydrofuran: Model compounds for the calcium complexation of oxidized sucrose

Meso- and ()-2,2′-bis(carboxymethoxy)oxydiacetic acid show superior calcium sequestering properties compared to sucrose-derived acetal polycarboxylate, due to extra steric hindrance.

Synthesis of Substituted 2,5-Dihydrothiophene-2-Carboxylic Acids by Lithium/Ammonia Reduction

Lithium/ammonia reduction of thiophene-2-carboxylic acid yields 2,5-dihydrothiophene-2-carboxylic acid, but its isolation is hindered by its susceptibility to further reduction or reductive cleavage.

Halogenation of Heterocycles: I. Five-Membered Rings

Halogenation of heterocycles can be achieved using electrophilic, nucleophilic, and radical processes, allowing for incorporation of other substituents and modifications to reactivity.

Anodic methoxylation of 2,5-dimethyl- and tetramethyl-thiophene. Formation and transformation of 2,5-dimethoxy adducts

Anodic methoxylation of 2,5-dimethyl- and tetramethyl-thiophene in methanol produces isomeric mixtures of 2,5-dimethoxy adducts, which can be transformed into 2-(methoxymethyl)thiophenes and thi

Concurrent anodic cyanation and methoxylation of methylated furans. Oxidation potential and reactivity, and stereochemical control of addition.

Concurrent anodic cyanation and methoxylation of methylated furans in MeOH reveals a linear correlation between reactivity and oxidation potential, with stereochemical control of addition being crucial for efficient reaction.

General Review of Proton Magnetic Resonance

Proton magnetic resonance (PMR) is a useful tool for studying kinetics and equilibrium in a variety of systems, including hydrogen bonding and molecular association.