109685-08-7Relevant academic research and scientific papers
Metalation of Phenols. Synthesis of Benzoquinones by the Oxidative Degradation Approach
Saa, Jose M.,Llobera, Antonia,Garcia-Raso, Angel,Costa, Antonio,Deya, Pedro M.
, p. 4263 - 4273 (2007/10/02)
In a effort to explore the potential of so-called oxidative degradation approach for the synthesis of quinones, we have investigated the direct metalation of a number of simple phenols such as o- and p-hydroxybenzyl alcohols, benzyl methyl ethers and N,N-dimethylbenzylamines.Apparently, only those phenolic substrates having available both a coordinating group for chelation and an electron-withdrawing group in a 1,3-relationship are efficiently lithiated, by the action of n-BuLi, in a regioselective manner.Those positions on the aromatic nucleus just flanked by a coordinating, or an acid-base, group could be metalated by action of the t-BuLi/THP system, in favorable cases.
A NOVEL DEGRADATIVE STRATEGY FOR THE SYNTHESIS OF p-QUINONES.
Saa, Jose M.,Morey, Jeronimo,Costa, Antonio
, p. 5125 - 5128 (2007/10/02)
p-Hydroxybenzylalcohols undergo Fremy's salt promoted degradative oxidation to give the corresponding p-benzoquinones.A novel strategy for the synthesis of p-benzoquinones based on the regioselective metalation of 2-methoxy-4-methoxymethyl phenols is presented.
