Modern Arene Chemistry || Arenetricarbonylchromium Complexes:Ipso,Cine,Tele Nucleophilic Aromatic Substitutions

✍ Scribed by Astruc, Didier

• Publisher: Wiley-VCH Verlag GmbH & Co. KGaA
• Year: 2002
• Weight: 375 KB
• Category: Article
• ISBN-13: 9783527601769
• DOI: 10.1002/3527601767.ch11

✦ Synopsis

The complexation of an arene C 6 H 5 X to the tricarbonylchromium unit promotes addition of nucleophiles to the arene ring due to the strong electron-withdrawing ability of the Cr(CO) 3 group. If addition of the nucleophile Nu occurs at the carbon bearing the leaving group X, this is an overall ipso nucleophilic aromatic substitution S N Ar. If addition of the nucleophile takes place on another carbon, the anionic h 5 -X-cyclohexadienyltricarbonylchromium intermediates can be treated with acid giving h 4 -X-cyclohexadiene derivatives via chromium hydride intermediates. The driving force of these reactions is the elimination of HX. These reactions are called cine and tele S N Ar. In this chapter, an overview of these S N Ar substitutions is presented as well as recent developments relating to organic synthesis.

11. 1

Scheme 1. Effects of the Cr(CO) 3 entity on the arene ring.