Issue 4, 2006
From the journal:

Chemical Communications

Building an extended inverse crown motif via alkali-metal-mediated α-magnesiation of furan

David V. Graham,a   Eva Hevia,a   Alan R. Kennedy,a   Robert E. Mulvey,*a   Charles T. O'Haraa  and  Christine Talmard†a  

* Corresponding authors

a WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow, UK
E-mail: r.e.mulvey@strath.ac.uk

Abstract

The utility of inverse crown chemistry is extended to aromatic heterocycles, as furan is deprotonated selectively at the α-position by the mixed-metal alkyl-amido base [(TMEDA)·Na(Bun)(TMP)Mg(TMP)] to generate a transient intermediate which undergoes disproportionation to the disodium dimagnesium hexafuryl tri(thf) complex [{{(thf)3·Na2}{(TMEDA)·Mg2}(2-C4H3O)6}∞], a new type of inverse crown structure with triply-stabilized (through Mg–C σ, Na–O σ and Na⋯C–C π interactions) furyl ‘guest’ anions, and the tris(amide) [(TMEDA)x·NaMg(TMP)3].

Graphical abstract: Building an extended inverse crown motif via alkali-metal-mediated α-magnesiation of furan

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/B514985A
Article type
Communication
Submitted
24 Oct 2005
Accepted
08 Nov 2005
First published
02 Dec 2005

Chem. Commun., 2006, 417-419

Permissions

Request permissions

Building an extended inverse crown motif via alkali-metal-mediated α-magnesiation of furan

D. V. Graham, E. Hevia, A. R. Kennedy, R. E. Mulvey, C. T. O'Hara and C. Talmard, Chem. Commun., 2006, 417 DOI: 10.1039/B514985A

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