63485-25-6Relevant articles and documents
Chemoselective oxidative generation of ortho-quinone methides and tandem transformations
Ishihara, Kazuaki,Kondo, Ryutaro,Nishioka, Kohei,Uyanik, Muhammet
, p. 353 - 362 (2020/04/09)
ortho-Quinone methides are useful transient synthetic intermediates in organic synthesis. These species are most often generated in situ by the acid- or base-mediated transformation of phenols that have been pre-functionalized at a benzylic position, or by biomimetic oxidation of the corresponding ortho-alkylphenols with metal oxidants or transition-metal complexes. Here we describe a method for the transition-metal-free oxidative generation of o-QMs from ortho-alkylarenols, using hypoiodite catalysis under nearly neutral conditions, which can then be applied in one-pot tandem reactions. This method for the chemoselective oxidative generation of ortho-quinone methides may prove superior to previous methods with respect to environmental issues and scope, and can be applied to various tandem reactions such as inter- or intramolecular [4 + 2] cycloaddition, oxa-6π-electrocyclization, conjugate addition and spiroepoxidation. [Figure not available: see fulltext.].
Selective copper(II)-mediated oxidative coupling of a nucleophilic reagent to the para-methyl group of 2,4,6-trimethylphenol
Boldron, Christophe,Oezalp-Yaman, Seniz,Gamez, Patrick,Tooke, Duncan M.,Spek, Anthony L.,Reedijk, Jan
, p. 3535 - 3541 (2007/10/03)
A copper(II) neocuproine system has been developed for the efficient and very selective 1,6-addition of a nucleophile to the para-methyl group of 2,4,6-trimethylphenol. Crystallographic and spectroscopic data point towards the involvement of a μ-methoxo-μ-phenoxo-bridged copper species which appears to generate a highly reactive quinone methide intermediate that can be attacked by a nucleophilic reagent. The Royal Society of Chemistry 2005.