Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 15, Pages 6574-6582Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo301185h
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Funding
- National Institutes of Health [GM062924, 1S10RR031789-01]
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Chromenes and isochromenes react quickly with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) to form persistent aromatic oxocarbenium ions through oxidative carbon-hydrogen cleavage. This process is tolerant of electron-donating and electron-withdrawing groups on the benzene ring and additional substitution on the pyran ring. A variety of nucleophiles can be added to these cations to generate a diverse set of structures.
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