Demethylation of aryl methyl ethers

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TET enzymes are dioxygenases in the family of alpha-ketoglutarate-dependent hydroxylases. The TET active site contains a highly conserved triad motif, in which the catalytically-essential Fe II is held by two histidine residues and one aspartic acid residue see figure. Demethylation of some sterols are steps in the biosynthesis of testosterone and cholesterol. Methyl groups are lost as formate. Cleaving methyl ethers[ edit ] Aryl methyl ethers are pervasive in lignin and many derived compounds.

The reaction typically requires harsh conditions or harsh reagents. This is followed by SN2 attack of the arylmethyloxonium ion at the methyl group by either pyridine or chloride ion depending on the substrate to give the free phenol and, ultimately, N-methylpyridinium chloride, either directly or by subsequent methyl transfer from methyl chloride to pyridine. A slightly milder set of conditions uses cyclohexyl iodide CyI, The mechanism of ether dealkylation proceeds via the initial reversible formation of a Lewis acid-base adduct between the strongly Lewis acidic BBr3 and the Lewis basic ether.

Retention of stereochemistry is observed. Partial demethylative oxidation is feasible, as shown in the preparation of several intramolecular quinhydrones eq 5 and a precursor of daunomy-cinone. In a synthesis of methoxatin eq 6 the o- quinone moiety was generated from an aryl methyl ether.

This reaction was utilized to form the quinoline-containing alkaloid natural product , atanine, from the Rutaceae family. Zhou, S. Zheng, G. He, J. Li, L. He, and D. BeL Lithium chloride -catalyzed selective demethylation of aryl methyl ethers under microwave irradiation. Journal of Molecular Catalysis A Chemical 1—2 16— Some aliphatic ethers can be cleaved by thallium iii nitrate in acetic anhydride.

New reagents for the demethylation of aryl methyl ethers include the stable, crystalline, and easily handled complexes of boron halides BBr3 and BCI3 with dimethyl sulphide,and the salt obtained from treatment of N-methylaniline with sodium hydride in HMPA.

The latter system cleaves methyl aryl ethers more readily than benzyl aryl ethers. Aryl methyl ethers can be cleaved by heating with EtS