Title of article
2-Alkoxyarenol-derived orthoquinols in carbon–oxygen, carbon–nitrogen and carbon–carbon bond-forming reactions
Author/Authors
Stéphane Quideau، نويسنده , , Laurent Pouységu، نويسنده , , Mayalen Oxoby، نويسنده , , Matthew A Looney، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2001
Pages
11
From page
319
To page
329
Abstract
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.
Keywords
Phenol oxidation , arenol , dearomatization , orthoquinone monoketals , oxidative nucleophilic substitution , orthoquinol acetates , cyclohexa-2 , 4-dienones , diaryl ether , Heterocyclization , hypervalent iodine
Journal title
Tetrahedron
Serial Year
2001
Journal title
Tetrahedron
Record number
1081589
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