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Multiple Reaction Pathways between the Carbanions of α‐Alkoxy‐α‐phenylacetonitrile and o ‐Chloronitrobenzene
Author(s) -
Mąkosza Mieczysław,
Sulikowski Daniel
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100909
Subject(s) - chemistry , carbanion , adduct , alkoxy group , reagent , medicinal chemistry , chlorine , selectivity , stereochemistry , organic chemistry , catalysis , alkyl
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.