A mild thermal and acid-catalyzed rearrangement of O-aryl ethers into ortho-hydroxy arenes.
[reaction: see text] An unusual rearrangement of an O-aryl ether to an ortho-hydroxyaryl system was discovered during our studies on the synthesis of diazonamide A. We discuss the exploration of this rearrangement under mild thermal and both Brønsted and Lewis acid-catalyzed conditions.
Goldberg
Frederick W
FW
Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, Texas 78712, USA.
Magnus
Philip
P
Turnbull
Rachel
R
D000143:Acids / Q000737:chemistry*; D002384:Catalysis; D004987:Ethers / Q000737:chemistry*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry; D006900:Hydroxylation; D015394:Molecular Structure; D010080:Oxazoles / Q000737:chemistry; D013696:Temperature
D000143:Acids; D004987:Ethers; D006576:Heterocyclic Compounds, 4 or More Rings; D010080:Oxazoles