Journal
NEW JOURNAL OF CHEMISTRY
Volume 36, Issue 5, Pages 1141-1144Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c2nj40021a
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Funding
- U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences [DE-SC00001055]
- Center for Electrocatalysis, Transport Phenomena, and Materials (CETM) for Innovative Energy Storage, an Energy Frontier Research Center
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C-H activation of the methyl group of toluene and related ArCH3 derivatives by 2,3-dichloro-4,5-dicyano-1,4-benzoquinone (DDQ) gives insertion products, ArCH2O[C6Cl2-(CN)(2)]OH via a rate-determining hydride abstraction by DDQ. The resulting benzylic ether can undergo reactions with phosphines to give benzylic phosphonium salts (Wittig reagents) and with phosphites to give phosphonate esters (Horner-Wadsworth-Emmons reagents).
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