Direct access to β-oxodiazo compounds by copper(II)-catalyzed oxidative rearrangement of stabilized vinyl diazo derivatives
The copper(II)-catalyzed reaction of alkenyldiazo compounds with iodosylbenzene leading to β-oxodiazo derivatives is reported. This process occurs via an unprecedented 1,2-shift of the diazoacetate function. A selection of the synthetic applications of a
Barluenga, Jose,Lonzi, Giacomo,Riesgo, Lorena,Tomas, Miguel,Lopez, Luis A.
supporting information; experimental part
p. 18138 - 18141
(2011/12/21)
Formation of five-membered cyclic orthoesters from tribromides with participation of a neighboring carbonyl group
The Mg-mediated conjugate addition of bromoform to enones followed by alcoholysis of the resulting keto tribromides proceeds through an unusual course, affording cyclic orthoester (dihydrofuran) intermediates under neutral workup conditions. However, acid
Gururaja, Guddeangadi N.,Mobin, Shaikh M.,Namboothiri, Irishi N. N.
experimental part
p. 2048 - 2052
(2011/05/16)
Practical synthesis of diethyl phenylsuccinate by Mg-promoted carboxylation of ethyl cinnamate
Mg-promoted reduction of ethyl cinnamate (1a) in the presence of carbon dioxide gave a mixture of β-carboxylated compound 2a and α,β-dicarboxylated compound 3a. Similar reductive carboxylation of 1a followed by acidic decarboxylation of one of the two geminal carboxyl groups of the generated 3a and esterification afforded selective formation of diethyl phenylsuccinate (2a) in good yield.