719272-47-6Relevant articles and documents
trans-Stereoselective intramolecular crossed pinacol coupling of aromatic 1,4-, 1,5-, and 1,6-diketones by electroreduction
Kise, Naoki,Shiozawa, Yousuke,Ueda, Nasuo
, p. 7599 - 7603 (2004)
Electroreduction of aromatic 1,4-, 1,5-, and 1,6-diketones in the presence of chlorotrimethylsilane and triethylamine gave four-, five-, and six-membered 1,2-diols with trans-stereoselectivity.
Unexpected TiIII/Mn-promoted pinacol coupling of ketones
Paradas, Miguel,Campana, Araceli G.,Estevez, Rosa E.,De Cienfuegos, Luis Alvarez,Jimenez, Tania,Robles, Rafael,Cuerva, Juan M.,Oltra, J. Enrique
experimental part, p. 3616 - 3619 (2009/09/06)
Titanocene(III) chemistry has emerged in the last decades as an indispensable tool in C-C bond-forming reactions. In this context, pinacol and related reactions allow the stereoselective synthesis of vicinal diols. In this work, we present new applications of these reactions using as starting materials aromatic ketones. Simple and smooth reaction conditions have been developed and have been applied for inter- and intramolecular processes. We also describe that although Cp2TiCl is usually used as a monoelectronic reducing agent, it can be also used as an efficient Lewis acid.
Oxidative Cleavage of vic-Diols Using Copper(II) Bromide-Lithium t-Butoxide: A New Route to Unsymmetrical 1,5- and 1,6-Diketones
Fujiwara, Tooru,Tsuruta, Yumiko,Arizono, Ko-Ichi,Takeda, Takeshi
, p. 962 - 964 (2007/10/03)
Unsymmetrical 1,6-diketones were obtained by the copper(II) bromide-lithium t-butoxide oxidation of 1,2-disubstituted 1,2-cyclohexanediols. The diols were easily prepared by the addition of Grignard reagents to 2-trimethylsiloxy-2-cyelohexenone followed by the hydrolysis and treatment of the resulting 2-hydroxycyclohexanones with the second Grignard reagents. Similarly, 1,5-Diketones were obtained using 2-trimethylsiloxy-2-cyclopentenone as a starting material.