Issue 80, 2019

A newly designed heterodiene and its application to construct six-membered heterocycles containing an N–O bond

Abstract

A new type of zwitterionic nitrosoalkene generated in situ from dehydrohalogenation of α-halo-N-alkylhydroxamic acids was designed. [4+2] cycloadditions of this heterodiene to olefins provide a facile route to construct six-membered heterocycles containing an N–O bond and a new protocol for 1,2-syn carbohydroxylate alkenes with a hydroxyl and acetamide group. DFT calculations support a concerted cycloaddition pathway and the solvent HFIP can stabilize the transition state through H-bonding interaction.

Graphical abstract: A newly designed heterodiene and its application to construct six-membered heterocycles containing an N–O bond

Supplementary files

Article information

Article type
Communication
Submitted
08 Aug 2019
Accepted
12 Aug 2019
First published
12 Aug 2019

Chem. Commun., 2019,55, 12012-12015

A newly designed heterodiene and its application to construct six-membered heterocycles containing an N–O bond

W. Ji, C. Li, H. Chen, Z. Yu and X. Liao, Chem. Commun., 2019, 55, 12012 DOI: 10.1039/C9CC05694G

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