Issue 12, 2018

A combined density functional theory and numerical simulation investigation of levels of chirality transfer and regioselectivity for the radical cyclizations of N-methyl-, N-ethyl- and N-isopropyl-substituted ortho-halo-N-acryloylanilides

Abstract

In this study, we employed density functional theory and numerical simulation methods to investigate the mechanism of intramolecular radical cyclization reactions of ortho-halo-N-acryloylanilides bearing N-alkyl substituents, namely, methyl, ethyl, and isopropyl. We established kinetic differential equations for elementary reaction pathways on the constructed potential energy profiles and performed numerical simulation computations. Using theoretically computed kinetic and thermodynamic data and numerically simulated regio- and stereochemistry, we revealed the detailed mechanism and memory of chirality of the investigated cyclization reactions. Furthermore, the levels of chirality transfer of ortho-halo-N-acryloylanilides with N-alkyl substituents larger in volume than isopropyl were numerically calculated. The computed results provided insight into the construction of nitrogen-containing heterocyclic compounds via the intramolecular radical cyclization approach using N-alkyl-substituted ortho-halo-N-acryloylanilide derivatives as the substrates.

Graphical abstract: A combined density functional theory and numerical simulation investigation of levels of chirality transfer and regioselectivity for the radical cyclizations of N-methyl-, N-ethyl- and N-isopropyl-substituted ortho-halo-N-acryloylanilides

Supplementary files

Article information

Article type
Paper
Submitted
07 Mar 2018
Accepted
21 Apr 2018
First published
24 Apr 2018

New J. Chem., 2018,42, 9783-9790

A combined density functional theory and numerical simulation investigation of levels of chirality transfer and regioselectivity for the radical cyclizations of N-methyl-, N-ethyl- and N-isopropyl-substituted ortho-halo-N-acryloylanilides

X. Wang, L. Yuan, C. Jia, H. Qu, B. Li, Y. Chi and H. Yu, New J. Chem., 2018, 42, 9783 DOI: 10.1039/C8NJ01102H

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