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Unprecedented McMurry Reactions with Acylsilanes: Enedisilane Formation versus Brook Rearrangement

MPS-Authors
http://pubman.mpdl.mpg.de/cone/persons/resource/persons58380

Fürstner,  Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons58992

Seidel,  Günter
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons58558

Gabor,  Barbara
Service Department Mynott (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

Kopiske,  Carsten
Service Department Krüger (XRAY), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons58723

Krüger,  Carl
Service Department Krüger (XRAY), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons58838

Mynott,  Richard
Service Department Mynott (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

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.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0014-A3BC-9
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.