Calcium carbide: Highly potent solid reagent for the construction of heterocycles

Tetrahedron, Journal Year: 2023, Volume and Issue: 149, P. 133720 - 133720

Published: Nov. 1, 2023

Language: Английский

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Vinylation of Alcohols, Thiols, and Nitrogen Compounds Using a Stoichiometric Amount of In Situ Generated Acetylene

Organics, Journal Year: 2025, Volume and Issue: 6(1), P. 5 - 5

Published: Feb. 8, 2025

In this work, we developed a highly efficient and versatile environmentally benign methodology for the vinylation of broad scope substances, including alcohols, thiols, nitrogen compounds. The key advantage proposed method is use calcium carbide as robust acetylene source in stoichiometric ratio to substrates. Lacking requirement excess, protocol safe, economic, limits waste production. procedure allows large variety O-,S-,N-vinyl compounds be synthesized up quantitative yields. Our scalable, allowing us obtain vinyl derivatives Gram-scale quantities. We also demonstrated significant synthetic value our approach by performing label-economic synthesis 13C2-labeled using carbide-13C2. well-optimized process, conversion Ca13C2 reached 89%.

Language: Английский

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Proximity effects: Structural implications and quantum-chemical description. Review

Journal of Molecular Structure, Journal Year: 2024, Volume and Issue: 1310, P. 138283 - 138283

Published: April 11, 2024

Proximity effects occur between vicinal functional groups or a group and specific molecular fragment in close proximity, for example an endocyclic N atom the ortho position relative to group. They are combination of through-bond inductive resonance effects, through-space interactions, which can be either attractive repulsive. In this review, we discuss quantum-chemical tools examples from literature that explore structural physicochemical implications proximity effects. We focus on derivatives small molecules: benzene, polycyclic aromatic hydrocarbons, simple heterocycles, lastly, purine derivatives.

Language: Английский

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[3 + 2] Cycloaddition of nitrile oxides to dichloropropenes and 1,3‐dichlorobut‐2‐ene: A regioselectivity issue

Journal of Heterocyclic Chemistry, Journal Year: 2024, Volume and Issue: 61(4), P. 556 - 567

Published: Jan. 24, 2024

Abstract The reaction of nitrile oxides with 2,3‐dichloroprop‐1‐ene, 1,3‐dichloroprop‐1‐ene, and 1,3‐dichlorobut‐2‐ene leads to 5‐(chloromethyl)isoxazoles, 4‐(chloromethyl)isoxazoles, or mixtures both regioisomers. direction cycloaddition reactivity substrate is determined by the steric hindrance at terminal carbon atom alkene double bond. It has been found that isomeric products 1,3‐dichloropropene have significantly different dehydrochlorination capabilities. experimental data on regioselectivity relative substrates are in agreement results quantum chemical calculations.

Language: Английский

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Base-Free Fluoride-Mediated Vinylation of Alcohols with Calcium Carbide

Russian Journal of General Chemistry, Journal Year: 2024, Volume and Issue: 94(12), P. 3155 - 3163

Published: Dec. 1, 2024

Language: Английский

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