110598-38-4Relevant academic research and scientific papers
Diethylaluminum chloride mediated vinylsilane synthesis: Comparison of different solvent systems
Kwan, Man Lung,Battiste, Merle A.,Macala, Megan K.,Aybar, Sylvia C.,James, Nicholas C.,Haoui, Joseph J.
, p. 1943 - 1950 (2004)
Aromatic ketones were converted to one-carbon elongated-vinylsilanes in a convenient one-pot operation via the Peterson protocol. Reactions were conducted in two different solvents for comparison: pentane and triethylamine. Results indicate that triethylamine appeared to be a more suitable solvent for such a transformation producing vinylsilanes with great chemo- and stereo-selectivity than pentane.
A convenient one-pot, organoaluminum mediated vinylsilane synthesis from non-enolizable ketones via the Peterson protocol
Kwan, Man Lung,Battiste, Merle A
, p. 8765 - 8768 (2002)
Vinylsilanes serve as convenient vinyl anion equivalents which have gained popularity over decades. A variety of non-enolizable aromatic ketones are converted to the corresponding vinylsilanes in a one-pot procedure involving the addition of (trimethylsilylmethyl)lithium to aromatic ketones followed by addition of diethylaluminum chloride and then small amounts of water. Halide and alkoxide substituents are tolerated, and this trans-stereoselective (broad generalization; the most sterically bulky group on the double bond is trans to the trimethylsilyl group) reaction affords vinylsilanes in good yield.
Selenobenzophenones and diazoalkanes: Isolation of tetraarylethylenes by the reaction of benzophenone hydrazones with diselenium dibromide
Okuma, Kentaro,Kojima, Kazuki,Oyama, Kosuke,Kubo, Kento,Shioji, Kosei
, p. 820 - 825 (2007/10/03)
The reaction of selenobenzophenones with diazomethane afforded the corresponding diarylethylenes and symmetrical olefins. The reaction with diaryldiazomethanes gave three different types of tetraarylethylenes. This reaction proceeded through 1,3,4-selenadiazoline intermediates, and retrocyclization was observed. The formation of 1,3,4-selendiazolines was independently confirmed by the reaction of benzophenone hydrazones with diselenium dibromide, which afforded tetraarylethylenes in good yields. This method is applicable to the two-step synthesis of tetraarylethylenes from benzophenones. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
SELENOBENZOPHENONES AND DIAZOALKANES: REACTION AND MECHANISTIC ELUCIDATION
Okuma, Kentaro,Kojima, Kazuki,Ohta, Hiroshi
, p. 259 - 262 (2007/10/02)
The reaction of selenobenzophenones with diazomethane, afforded the corresponding diarylethylenes and symmetrical olefins.The reaction with other diazoalkanes gave three different types of olefins.This reaction proceeded through selenadiazoline intermediates and retrocyclization was observed.Keywords: Selenobenzophenone; diazoalkane; selenadiazoline; episelenide; olefin.
PALLADIUM-CATALYSED REDUCTIVE ADDITION OF ARYL IODIDES TO ARYL AND ALKYLETHYNYLSILANES: A STEREO AND REGIOSELECTIVE ROUTE TO FUNCTIONALIZED 2,2-DISUBSTITUTED VINYLSILANES
Arcadi, A.,Cacchi, S.,Marinelli, F.
, p. 6397 - 6400 (2007/10/02)
Aryl and alkylethynylsilanes are converted into 2,2-disubstituted vinylsilanes containing various common functional groups in the presence of aryl iodides, a palladium catalyst, formic acid, and a tertiary or secondary amine with high stereoselectivity an
