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  Unprecedented McMurry Reactions with Acylsilanes: Enedisilane Formation versus Brook Rearrangement

Fürstner, A., Seidel, G., Gabor, B., Kopiske, C., Krüger, C., & Mynott, R. (1995). Unprecedented McMurry Reactions with Acylsilanes: Enedisilane Formation versus Brook Rearrangement. Tetrahedron, 51(32), 8875-8888. doi:10.1016/0040-4020(95)00482-N.

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 Creators:
Fürstner, Alois1, Author           
Seidel, Günter1, Author           
Gabor, Barbara2, Author           
Kopiske, Carsten3, Author
Krüger, Carl3, Author           
Mynott, Richard2, Author           
Affiliations:
1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              
2Service Department Mynott (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445627              
3Service Department Krüger (XRAY), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445624              

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 Abstract: The first inter- and intramolecular McMurry reactions of aroyltrimethylsilanes to substituted 1,2-bis(trimethylsilyl)ethene derivatives 2a-c and 7 are described. A low-valent titanium reagent prepared by the reduction of TiCl3 with Na on inorganic supports (Al2O3, NaCl, TiO2) turned out to be best suited. Depending on the reaction conditions and on the particular substitution patterns of the substrates, Brook rearrangements of the intermediate 1,2-disilylated titanium-1,2-diolates leading to the formation of C,O-disilyl-enol ethers may compete with the McMurry deoxygenation pathway.

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Language(s): eng - English
 Dates: 1995-05-081995-06-121995-08-07
 Publication Status: Published in print
 Pages: 14
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1016/0040-4020(95)00482-N
 Degree: -

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Title: Tetrahedron
  Other : Tetrahedron
Source Genre: Journal
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Publ. Info: Oxford : Pergamon
Pages: 14 Volume / Issue: 51 (32) Sequence Number: - Start / End Page: 8875 - 8888 Identifier: ISSN: 0040-4020
CoNE: https://pure.mpg.de/cone/journals/resource/954925448773