Matthew Aaron Looney

Matthew Aaron Looney
Texas Tech University | TTU · Department of Agricultural and Applied Economics

Master of Science

About

8
Publications
288
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258
Citations

Publications

Publications (8)
Article
Dearomatization of arenes is a powerful strategy for the preparation of functionalized cyclic olefins. Phenol oxidation can be exploited as a dearomatization tactic to produce cyclohexa-2,4-dienones. Iodine(III)-mediated oxidation of 2-alkyl- and 2-alkoxynaphthols was accomplished in the presence of an allylsilane or a silyl enol ether carbon-based...
Article
The λ3-iodane [bis(trifluoroacetoxy)]iodobenzene (BTI)-mediated oxidative dearomatization of 2-alkoxyarenols with soft external carbon-based nucleophiles constitutes a rapid access to highly functionalized naphthoid cyclohexa-2,4-dienones. These synthons can serve as valuable intermediates in the construction of the angularly-oxygenated benz[a]naph...
Article
Nitrogen-tethered 2-methoxyphenols are conveniently dearomatized into synthetically useful orthoquinol acetates by treatment with phenyliodine(III) diacetate in methylene chloride at low temperature. Subsequent fluoride- or base-induced intramolecular nucleophilic addition reactions furnish indole and quinoline derivatives. The potential of this me...
Article
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 presen...
Article
Full-text available
The non-dimerizing orthoquinone monoketal, 6-acetoxy-6-methoxy-3-methoxycarbonylcyclohexa-2,4-dienone, conveniently prepared from oxidative acetoxylation of its parent phenol with PhI(OAc)2 in CH2Cl2AcOH (3:1), cleanly undergoes 1,3-acetoxy migrations in the presence of silica gel at room temperature to furnish a 60:40 product mixture conceivably...

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