Work

Pull–Pull Halogenated β‐Cyanoacrylates in Aza‐Michael Reaction: Intriguing Problem of Regioselectivity

Year: 2025

Type: article

Abstract: The controlled regioselective addition of nitrogen‐centered nucleophiles to the pull–pull halogenated β‐cyanoacrylates is a challenging problem in the chemistry of pull–pull alkenes due to the close electronic properties of the vicinal acceptor groups. The influence of the type of halogen and its position on the double bond, as well as the amine nucleophilicity and the presence of additives on the direction of addition have been studied. The experimental data are in excellent agreement with the density functional theory (DFT) calculations.

Source: Asian Journal of Organic Chemistry

DOI: 10.1002/ajoc.202500414

Authors: Ilya A. Tyumentsev, Igor A. Ushakov, Anton V. Kuzmin, Alexander Yu. Rulev

Institutions: A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences

Language: English

Topic: Organic Chemistry Cycloaddition Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze

Funder: Siberian Branch, Russian Academy of Sciences

OpenAlex ID: W4413237830

FWCI: 0.297

Cites: 26

Cited by: 1

Related to: 10