The surprisingly facile thermal dehalogenation of chlorinated aromatics by a hydroaromatic donor solvent. Tautomerization of chlorinated phenols and anilines

P Mulder, IWCE Arends, D Santoro…

Index: Mulder, Peter; Arends, Isabel W. C. E.; Santoro, Danilo; Korth, Hans-Gert Journal of Organic Chemistry, 2003 , vol. 68, # 11 p. 4247 - 4257

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Citation Number: 12

Abstract

Up to 600 K, chlorinated benzenes and naphthalenes are inert in a hydrogen atom donating solvent such as 9, 10-dihydroanthracene. However, when a hydroxyl or amine group is attached to the 2 or 4 position relative to chlorine, a surprisingly facile and selective hydrodehalogenation occurs at temperatures between 530 and 630 K. These features are the result of the onset of tautomeric equilibria for the chlorophenols or-anilines, creating ...

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