43060-63-5Relevant academic research and scientific papers
Oxidative ortho-amino-methylation of phenols via C-H and C-C bond cleavage
Sun, Wenbo,Lin, Huacan,Zhou, Wenyu,Li, Zigang
, p. 7491 - 7494 (2014/02/14)
Initiated by CCl3Br, phenols undergo efficient ortho-selective oxidative cross dehydrogenative coupling (CDC) with trimethylamine. When tetramethylethylenediamine (TMEDA) is used instead of trimethylamine, oxidative carbon-carbon activation coupling (CAC) could occur to give the same salicylamines together with CDC by-products. These reactions are accelerated by a gold salt.
Controlled synthesis of novel dibenzene-1,2-diol mannich bases
Caulfield, Marcus J.,Russo, Tiziana,Solomon, David H.
, p. 545 - 549 (2007/10/03)
The synthesis of a number of novel dibenzene-1,2-diol Mannich bases can be achieved in good yields by the condensation of 2-methoxyphenol, formaldehyde and secondary diamines. The newly developed synthetic method utilizes 2-methoxyphenol instead of benzen
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.
