Issue 9, 2011
From the journal:

Organic & Biomolecular Chemistry

Fragmentations observed in the reactions of α-methoxy-γ-alkoxyalkyl iodide substrates with super-electron-donors derived from 4-DMAP and N-methylbenzimidazole†‡§

Ryan Sword,a   Luke A. Baldwina  and  John A. Murphy*a  

* Corresponding authors

a WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, United Kingdom
E-mail: john.murphy@strath.ac.uk
Tel: +44 (0)141 548 2389

Abstract

Reactions of super-electron-donors (SEDs) derived from 4-dimethylaminopyridine and from N-methylbenzimidazole with α-methoxy-γ-alkoxyalkyl iodides lead to liberation of the γ-alkoxy groups as their alcohols. This is consistent with generation of alkyl radicals from the alkyl halide precursors, and trapping of these radicals by the radical-cation of the SED, followed by a heterolytic fragmentation.

Graphical abstract: Fragmentations observed in the reactions of α-methoxy-γ-alkoxyalkyl iodide substrates with super-electron-donors derived from 4-DMAP and N-methylbenzimidazole

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Article information

DOI
https://doi.org/10.1039/C0OB01282C
Article type
Paper
Submitted
31 Dec 2010
Accepted
22 Feb 2011
First published
22 Feb 2011

Org. Biomol. Chem., 2011,9, 3560-3570

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Fragmentations observed in the reactions of α-methoxy-γ-alkoxyalkyl iodide substrates with super-electron-donors derived from 4-DMAP and N-methylbenzimidazole

R. Sword, L. A. Baldwin and J. A. Murphy, Org. Biomol. Chem., 2011, 9, 3560 DOI: 10.1039/C0OB01282C

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