98779-35-2Relevant academic research and scientific papers
A novel lanthanum metal-assisted reaction of diaryl ketones and electrophiles
Umeda, Rui,Ninomiya, Masashi,Nishino, Toshiaki,Kishida, Makoto,Toiya, Shunsuke,Saito, Tomoki,Nishiyama, Yutaka,Sonoda, Noboru
, p. 1287 - 1291 (2015/03/05)
A novel and efficient lanthanum metal-assisted carbon-carbon bond formation of diaryl ketones and various electrophiles, such as carbonyl compounds, esters, nitriles, and epoxides, has been developed. When diaryl ketones were allowed to react with dialkyl ketones in the presence of lanthanum metal and a catalytic amount of iodine, the cross pinacol coupling reaction proceeded to give the corresponding unsymmetrical 1,2-diols in moderate to good yields. α-Hydroxy ketones were prepared by the lanthanum metal-assisted reaction of diaryl ketones with esters or nitriles, followed by hydrolysis with aq HCl. It is interesting to note that for the epoxides, the coupling reaction proceeded via the Meinwald rearrangement of epoxides to give the corresponding 1,2-diols.
Retropinacol/cross-pinacol coupling reactions - A catalytic access to 1,2-unsymmetrical diols
Scheffler, Ulf,Stoesser, Reinhard,Mahrwald, Rainer
supporting information, p. 2648 - 2652,5 (2012/12/12)
A new concept to access unsymmetrical 1,2-diols with high yields is reported. This new methodology is based on a retropinacol/cross-pinacol coupling process. This transformation is characterized by its operational simplicity and very mild reaction condi tions.
The Formation of an Enantiomerically Pure Product of Free Radical Coupling. The Chemistry of Diphenylcarbene in Polycrystalline (S)-(+)-2-Butanol
Zayas, Jose,Platz, Matthew S.
, p. 7065 - 7069 (2007/10/02)
Photolysis of 0.1 M diphenyldiazomethane at 77 K or 137 K in solid (S)-(+)-2-butanol gives tertiary alcohol 9 along with other products.Compound 9 was isolated and found to be enantiomerically pure by chiral NMR shift reagents.Compound 9 is formed by reaction of triplet diphenylcarbene with (S)-(+)-2-butanol to give a radical pair which subsequently collapses.The solid-state matrix directs the radical pair collapse with complete retention of configuration.
