Synthesis of polysubstituted benzenes via the tandem addition-rearrangement aryne reaction of substituted 2-bromoanisoles and lithioarenenitriles

SP Khanapure, L Crenshaw, RT Reddy…

Index: Khanapure, Subhash P.; Crenshaw, Lori; Reddy, R. Thimma; Biehl, Edward R. Journal of Organic Chemistry, 1988 , vol. 53, # 21 p. 4915 - 4919

Full Text: HTML

Citation Number: 16

Abstract

Lithioarenenitriles add regiospecifically to substituted 3-methoxybenzynes generated in situ from the corresponding haloarenes by wing lithium diisopropylamide as a base. The addition to methoxybenzynes substituted with an electron-releasing group is followed by rearrangement to substituted 2-cyano-3-(arylmethyl) anisoles. The rearrangement pathway involves cyclization of the initially formed nitrile-aryne adducts to benzocyclobutanone ...