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Anodic Oxidation: An Attractive Alternative to CAN‐Mediated Cleavage of para ‐Methoxyphenyl Ethers
Author(s) -
Vaxelaire Carine,
Souquet Florence,
Lannou MarieIsabelle,
Ardisson Janick,
Royer Jacques
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900262
Subject(s) - ceric ammonium nitrate , chemistry , anodic oxidation , cleavage (geology) , oxidative cleavage , ether , organic chemistry , anode , ammonium , combinatorial chemistry , catalysis , electrode , polymer , geotechnical engineering , grafting , fracture (geology) , engineering
para ‐Methoxyphenyl (PMP) ether is a very convenient protecting group for the alcohol function; however, its cleavage requires strong oxidative conditions. In this field, the use of powerful ceric ammonium nitrate has been widely described, despite the fact that its strong nature results in the formation of degradation products in acid‐ or oxidation‐sensitive substrates. In this paper, a new anodic oxidation method for the cleavage of para ‐methoxyphenyl ethers in weakly basic medium is reported. This process is an attractive alternative to circumvent the use of ceric ammonium nitrate. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)