Issue 36, 2013
From the journal:

Organic & Biomolecular Chemistry

Observation by NMR of cationic Wheland-like intermediates in the deiodination of protected 1-iodonaphthalene-2,4-diamines in acidic media†

Elvis A. Twum,a   Timothy J. Woodman,a   Wenyi Wangab  and  Michael D. Threadgill*a  

* Corresponding authors

a Medicinal Chemistry, Department of Pharmacy and Pharmacology, University of Bath, Claverton Down, Bath, UK
E-mail: m.d.threadgill@bath.ac.uk

b Department of Pharmacy, Shandong University, China

Abstract

1-Iodonaphthalene-2,4-diamines in trifluoroacetic acid/chloroform give stable Wheland-like tetrahedral cationic species observable by NMR, through an initial intramolecular protonation. Dynamic equilibria allow proton-deuterium exchange of aromatic protons and provide a mechanism for deiodination of 1-iodonaphthalene-2,4-diamines.

Graphical abstract: Observation by NMR of cationic Wheland-like intermediates in the deiodination of protected 1-iodonaphthalene-2,4-diamines in acidic media

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Article information

DOI
https://doi.org/10.1039/C3OB41386A
Article type
Paper
Submitted
05 Jul 2013
Accepted
05 Aug 2013
First published
07 Aug 2013

Org. Biomol. Chem., 2013,11, 6208-6214

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Observation by NMR of cationic Wheland-like intermediates in the deiodination of protected 1-iodonaphthalene-2,4-diamines in acidic media

E. A. Twum, T. J. Woodman, W. Wang and M. D. Threadgill, Org. Biomol. Chem., 2013, 11, 6208 DOI: 10.1039/C3OB41386A

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