Oxidative cleavage of benzylic and related ethers, using an oxoammonium salt

PP Pradhan, JM Bobbitt, WF Bailey

Index: Pradhan, Priya P.; Bobbitt, James M.; Bailey, William F. Journal of Organic Chemistry, 2009 , vol. 74, # 24 p. 9524 - 9527

Full Text: HTML

Citation Number: 40

Abstract

Benzylic ethers and related ArCH2OR substrates are oxidatively cleaved by 4-acetamido-2, 2, 6, 6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (1) in wet CH3CN at room temperature to give the corresponding aromatic aldehyde and alcohol in high yield. Primary or secondary alcohol products are further oxidized by 1 to give carboxylic acids and ketones, respectively. The oxidation likely involves a formal hydride abstraction from the benzylic ...

Related Articles:

… , characterization and use of 1, 3-disulfonic acid imidazolium hydrogen sulfate as an efficient, halogen-free and reusable ionic liquid catalyst for the trimethylsilyl …

[Shirini, Farhad; Khaligh, Nader Ghaffari; Akbari-Dadamahaleh, Somayeh Journal of Molecular Catalysis A: Chemical, 2012 , vol. 365, p. 15 - 23]

Oxidations by methyl (trifluoromethyl) dioxirane. 2. Oxyfunctionalization of saturated hydrocarbons

[Mello, Rossella; Fiorentino, Michele; Fusco, Caterina; Curci, Ruggero Journal of the American Chemical Society, 1989 , vol. 111, # 17 p. 6749 - 6757]

Oxidations by methyl (trifluoromethyl) dioxirane. 3. Selective polyoxyfunctionalization of adamantane

[Tetrahedron Letters, , vol. 31, # 21 p. 3067 - 3070]

Catalytic activity of a polymerizable tris (β-ketoesterate) iron (III) complex towards the oxidation of organic substrates

[Mastrorilli, Piero; Nobile, Cosimo Francesco Tetrahedron Letters, 1994 , vol. 35, # 24 p. 4193 - 4196]

Highly selective N-and O-functionalization of adamantane utilizing nitrogen oxides. Kyodai-nitration of aliphatic hydrocarbons

[Suzuki, Hitomi; Nonoyama, Nobuaki Chemical Communications, 1996 , # 15 p. 1783 - 1784]

More Articles...