Issue 20, 2002
From the journal:

Chemical Communications

5-Azahexenoyl radicals cyclize via nucleophilic addition to the acyl carbon rather than 5-exo homolytic addition at the imine

Chantal T. Falzon,a   Ilhyong Ryub  and  Carl H. Schiesser*a  

* Corresponding authors

a School of Chemistry, Bio21 Institute of Molecular Science and Biotechnology, The University of Melbourne, Victoria, Australia
E-mail: carlhs@unimelb.edu.au

b Department of Chemistry, Faculty of Arts and Sciences, Osaka Prefecture University, Sakai, Osaka 599-8531, Japan

Abstract

Molecular orbital calculations predict that the 5-azahexenoyl radical ring closes via nucleophilic addition to the acyl carbon to afford the 5-exo product; CCSD(T)/cc-pVDZ//BHLYP/cc-pVDZ calculations predict energy barriers of 36.1 and 46.9 kJ mol−1 for the exo and endo cyclization modes of the 5-azahexenoyl radical, respectively.

Graphical abstract: 5-Azahexenoyl radicals cyclize via nucleophilic addition to the acyl carbon rather than 5-exo homolytic addition at the imine

About
Cited by
Related
Download options Please wait...

Article information

DOI
https://doi.org/10.1039/B207729A
Article type
Communication
Submitted
07 Aug 2002
Accepted
04 Sep 2002
First published
18 Sep 2002

Chem. Commun., 2002, 2338-2339

Permissions

Request permissions

5-Azahexenoyl radicals cyclize via nucleophilic addition to the acyl carbon rather than 5-exo homolytic addition at the imine

C. T. Falzon, I. Ryu and C. H. Schiesser, Chem. Commun., 2002, 2338 DOI: 10.1039/B207729A

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