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

R.E. Mulvey, V.L. Blair, William Clegg, A.R. Kennedy, J. Klett, L. Russo

Research output: Contribution to journalArticle

87 Citations (Scopus)

Abstract

The cleavage of ethers is commonly encountered in organometallic chemistry though rarely studied in the context of newly emerging bimetallic reagents. Recently it was reported that a bimetallic sodium-zinc base can deprotonate cyclic tetrahydrofuran (THF) under mild conditions without opening its heterocyclic (OC4) ring. In marked contrast to this synergic sedation, herein we show that switching to more reactive sodium-magnesium or sodium-manganese bases promotes cleavage of at least six bonds in THF, but the ring fragments are uniquely captured in separate crystalline complexes. Oxide fragments occupy guest positions in bimetallic inverse crown ethers and C4 fragments ultimately appear in bimetallated butadiene molecules. These results demonstrate the special synergic reactivity that can be executed by bimetallic reagents, including the ability to capture and control and thereby study reactive fragments from sensitive substrates.
LanguageEnglish
Pages588-591
Number of pages4
JournalNature Chemistry
Volume2
DOIs
Publication statusPublished - May 2010

Fingerprint

Sodium
Crown Ethers
Crown ethers
Ethers
Organometallics
Manganese
Butadiene
Oxides
Magnesium
Zinc
Crystalline materials
Molecules
Substrates
tetrahydrofuran
1,3-butadiene

Keywords

  • inorganic chemistry
  • organometallic chemistry
  • THF
  • cyclic tetrahydrofuran

Cite this

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Cleave and capture chemistry illustrated through bimetallic-induced fragmentation of tetrahydrofuran. / Mulvey, R.E.; Blair, V.L.; Clegg, William; Kennedy, A.R.; Klett, J.; Russo, L.

In: Nature Chemistry, Vol. 2, 05.2010, p. 588-591.

Research output: Contribution to journalArticle

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AU - Mulvey, R.E.

AU - Blair, V.L.

AU - Clegg, William

AU - Kennedy, A.R.

AU - Klett, J.

AU - Russo, L.

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KW - organometallic chemistry

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