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Cleave and capture chemistry illustrated through bimetallic-induced fragmentation of tetrahydrofuran

Lookup NU author(s): Emeritus Professor Bill CleggORCiD, Dr Luca Russo

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Abstract

The cleavage of ethers is commonly encountered in organometallic chemistry, although rarely studied in the context of new, emerging bimetallic reagents. Recently, it was reported that a bimetallic sodium-zinc base can deprotonate cyclic tetrahydrofuran under mild conditions without opening its heterocyclic (OC4) ring. In marked contrast to this synergic sedation, herein we show that switching to the more reactive sodium-magnesium or sodium-manganese bases promotes cleavage of at least six bonds in tetrahydrofuran, but uniquely the ring fragments are captured in separate crystalline complexes. Oxide fragments occupy guest positions in bimetallic, inverse crown ethers and C-4 fragments ultimately appear in bimetallated butadiene molecules. These results demonstrate the special synergic reactivity that can be executed by bimetallic reagents, which include the ability to capture and control, and thereby study, reactive fragments from sensitive substrates.

Publication metadata

Author(s): Mulvey RE, Blair VL, Clegg W, Kennedy AR, Klett J, Russo L

Publication type: Article

Publication status: Published

Journal: Nature Chemistry

Year: 2010

Volume: 2

Issue: 7

Pages: 588-591

Print publication date: 23/05/2010

ISSN (print): 1755-4330

ISSN (electronic):

Publisher: Nature Publishing Group

URL: http://dx.doi.org/10.1038/NCHEM.667

DOI: 10.1038/NCHEM.667

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