Issue 18, 2020

Dimerization–cyclization reactions of isocyanoaryl-tethered alkylidenecyclobutanes via a triplet biradical mediated process

Abstract

A triplet biradical mediated dimerization–cyclization reaction of isocyanoaryl-tethered alkylidenecyclobutanes has been reported in this paper, giving a new protocol for the construction of macrocyclic skeletons including dihydroquinoline and quinoline units in moderate yields. The reaction proceeded through a key 1,4-diazabutatriene intermediate along with intramolecular redox to produce a biradical intermediate species, which subsequently experienced bond-breaking and -making processes to give the desired product. The reaction mechanism was supported by density functional theory (DFT) calculations.

Graphical abstract: Dimerization–cyclization reactions of isocyanoaryl-tethered alkylidenecyclobutanes via a triplet biradical mediated process

Supplementary files

Article information

Article type
Research Article
Submitted
23 jul 2020
Accepted
30 jul 2020
First published
31 jul 2020

Org. Chem. Front., 2020,7, 2634-2643

Dimerization–cyclization reactions of isocyanoaryl-tethered alkylidenecyclobutanes via a triplet biradical mediated process

L. Tao, Y. Wei and M. Shi, Org. Chem. Front., 2020, 7, 2634 DOI: 10.1039/D0QO00878H

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements