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 ...
Related Articles:
Phosphorus (V)-catalyzed deoxydichlorination reactions of aldehydes
[An, Jie; Tang, Xiaoping; Moore, Joshua; Lewis, William; Denton, Ross M. Tetrahedron, 2013 , vol. 69, # 41 p. 8769 - 8776]
[Chateauneuf, John E.; Liu, Michael T. H. Journal of the American Chemical Society, 1991 , vol. 113, # 17 p. 6585 - 6588]
[Chiang,Y.H. Journal of Organic Chemistry, 1971 , vol. 36, p. 2146 - 2155]
[Ibata, Toshikazu; Toyoda, Jiro; Liu, Michael T. H. Chemistry Letters, 1987 , p. 2135 - 2138]
[Chateauneuf, John E.; Liu, Michael T. H. Journal of the American Chemical Society, 1991 , vol. 113, # 17 p. 6585 - 6588]