Tetrahedron Letters

Mechanism of isomerization of ortho or para bromo phenols in superacids

JC Jacquesy, MP Jouannetaud

Index: Jacquesy, Jean-Claude; Jouannetaud; Marie-Paule Tetrahedron Letters, 1982 , vol. 23, # 16 p. 1673 - 1676

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Citation Number: 15

Abstract

In superacids ortho or para bromo phenols are isomerized into the meta bromo isomers. In SbF 5 -HF, the process is intramolecular and proceeds by a 1,2-Br shift. In CF 3 SO 3 H, the mechanism involves loss of bromine, followed by meta bromination. ... In superacid phenols ethers are more rapidly brominated than the corresponding phenols. ... Cherry G. , Culmann J.-C. , Sommer J.