The Journal of Organic Chemistry

Reactions of organic anions. 161. Dihalomethylation of nitroarenes via vicarious nucleophilic substitution of hydrogen with trihalomethyl carbanions

M Makosza, Z Owczarczyk

Index: Makosza, M.; Owczarczyk, Z. Journal of Organic Chemistry, 1989 , vol. 54, # 21 p. 5094 - 5100

Full Text: HTML

Citation Number: 84

Abstract

Trichlore and tribromomethyl carbanions generated by deprotonation of haloforms with potassium tert-butoxide in a THF-DMF mixture at ca.-70" C react with a variety of carbocyclic and heterocyclic nitroarenes according to the vicarious nucleophilic substitution scheme. The reaction provides an efficient and convenient way for the direct introduction of dihalomethyl substituents ortho and para to the nitro group, which in turn can be ...