54812-20-3Relevant 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.].
PREPARATION OF ALKYLARYLCARBINOLS BY MONO-OXIDATION AT THE BENZYLIC POSITION USING 2,3-DICHLORO-5,6-DICYANOBENZOQUINONE (D.D.Q.)
Bouquet, M.,Guy, A.,Lemaire, M.,Guette, J. P.
, p. 1153 - 1158 (2007/10/02)
A new and convenient method for the preparation of alkylarylacetates and alkylarylcarbinols is described.Monooxidation at the benzylic position was performed using 2,3-dichloro-5,6-dicyanobenzoquinone (D.D.Q.) in acetic acid.Good yields of arylcarbinols were obtained under mild conditions.