330581-67-4Relevant academic research and scientific papers
Electrochemical synthesis of dimerizing and nondimerizing orthoquinone monoketals
Deffieux, Denis,Fabre, Isabelle,Titz, Alexander,Leger, Jean-Michel,Quideau, Stephane
, p. 8731 - 8738 (2007/10/03)
Anodic oxidation of appropriately substituted 2-methoxyphenols or α-(2-methoxyphenoxy)-2-methylpropionic acids in the presence of methanol furnishes stable orthoquinone monoketals, and thus constitutes a valuable alternative to the use of chemical oxidants that are often based on toxic metallic species. The propionic acid derivatives are initially converted into O-spirolactonic quinone bisketals that are then selectively hydrolyzed into the desired monoketal compounds. In the absence of blocking substituents, orthoquinone monoketals spontaneously undergo Diels-Alder dimerizations into tricyclododecadienedienones with extraordinary site selectivity, regioselectivity, and stereoselectivity. Suggestions are made to open up a new track for a long awaited rationalization of these controls on the basis of the intramolecular [2 + 2] reactivity of these orthoquinone monoketal-derived cyclodimers.
2-Alkoxyarenol-derived orthoquinols in carbon-oxygen, carbon-nitrogen and carbon-carbon bond-forming reactions
Quideau, Stéphane,Pouységu, Laurent,Oxoby, Mayalen,Looney, Matthew A
, p. 319 - 329 (2007/10/03)
Silylated oxygen- and nitrogen-tethered orthoquinol acetates, generated by phenyliodine(III) diacetoxy-mediated oxidative acetoxylation of 2-alkoxyphenols in CH2Cl2 can be used to furnish regioselectively benzannulated heterocycles. Oxidative activation of 2-alkoxynaphthols with non-nucleophilic phenyliodine(III) bis(trifluoroacetoxy) in the presence of carbon nucleophiles, including oxidation sensitive silyl enol ethers, constitute a potentially valuable route to naturally occurring vicinally oxygenated benz[a]anthracene motifs.
