Multiple Reaction Pathways between the Carbanions of α-Alkoxy-α-phenylacetonitrile and o-Chloronitrobenzene

✍ Scribed by Mieczysław Mąkosza; Daniel Sulikowski

• Book ID: 102172210
• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: English
• Weight: 281 KB
• Volume: 2011
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.201100909

✦ Synopsis

Abstract

Carbanions of α‐methoxy‐ and α‐phenoxy‐α‐phenylacetonitriles undergo a variety of reactions with o‐chloronitrobenzene by initial formation of σ^H^ adducts and slower formation of σ^Cl^ adducts. Reversible formation of σ^H^ adducts followed by their fast transformation results in the formation of four different products with high selectivity. Slower addition in a position occupied by a chlorine atom to form σ^Cl^ adducts results in a conventional S~N~Ar reaction. These five reaction pathways are efficiently controlled by the conditions and additional reagents.