Synthesis of 2,6-Dihalo-4-nitro-N-alkylanilines by Aromatic Substitution of 2,6-Dihalo-4-nitro-arylethers

References

• Somani , P. , Bachand , R. T. , Murmann , W. and Almirante , L. 1966 . J. Med. Chem. , 9 : 823
   PubMed Web of Science ®Google Scholar
• Shechter , L. , Wynstra , J. and Kurkjy , R. P. 1956 . Ind. and Eng. Chem. , 48 ( 1 ) : 94
   Web of Science ®Google Scholar
• Burfield , D. R. , Gan , S. and Smithers , R. H. 1977 . JCS Perkin I , : 666
   Google Scholar
• Sandin , R. B. , Drake , W. V. and Leger , F. 1932 . Org. Synth. , XII : 28
   Google Scholar
• Miller , J. 1968 . “ Aromatic Nucleophilic Substitution ” . In Reaction mechanisms in Organic Chemistry , Monograph n°8 of the serie 206 Amsterdam : Elsevier . ch. 6
   Google Scholar
• Crampton , M. R. 1979 . Organic Reactions Mechanisms , 255 New-York : John Wiley & Sons .
   Google Scholar
• Brooke , G. M. 1979 . Aromatic and Heteroaromatic Chemistry , 287 London : the Chemical Society . Specialist Pariodical Reports
   Google Scholar
• Silverstein , R. M. and Bassler , G. C. 1968 . Identification spectrométrique des composés organiques , 34 Paris : Masson .
   Google Scholar
• Cahn , N. B. R. S. J. Chem. Soc. , 1931 1121 had already observed cases of dealkylation of phenyl-ethers by amines, but these involved polynitro aromatic substrates
   Google Scholar
• Jung , M. E. and Lyster , M. A. 1977 . J. Org. Chem. , 42 ( 23 ) : 3761
   Web of Science ®Google Scholar
• Ahmad , R. , Saa , J. M. and Cava , M. P. 1977 . J. Org. Chem. , 42 ( 7 ) : 1228
   PubMed Web of Science ®Google Scholar
• Harrison , I. T. JCS, Chem. Comm. , 1969 616
   Google Scholar
• Feutrill , G. I. and Mirrington , R. N. Tetrahedron Letters , 1970 ( 16 ) 1327
   Google Scholar
• Mc , C AR , Thy , J. R. , Moore , J. L. and Gregge , R. J. Tetrahedron Letters , 1978 ( 52 ) 5183
   Google Scholar
• McOMI , E. J. F. W. 1973 . Protective Groups in Organic Chemistry , New-York : Plenum Press . ch. 4, 145.
   Google Scholar
• Greene , T. W. 1981 . Protective Groups in Organic Chemistry , John Wiley & Sons .
   Google Scholar
• Barton , D. B. and Ollis , W. D. 1979 . Comprehensive Organic Chemistry , Vol. 1 , 897 Pergamon Press . ch. 4 (5)
   Google Scholar
• Melting points measured using a METTLER FPI “capillary tube” type instrument. NMR spectra were recorded using a JEOL PMX 60 instrument at 60 MHz. Chemical shifts of compounds in CDCl3 are given in ppm relative to tetramethylsilane (TMS = 0). Mass spectra were obtained from the analytical chemistry department (Prof. Cl. Quincy) of the Faculty of Pharmacy, Université Claude Bernard, Lyon. All new compounds (3, 4, 5 and 6) gave elemental analysis values (C,H,N) within ± 0,3% of those calculated
   Google Scholar
• Block , P. Jr and Powel , G. 1942 . J. Amer. Chem. Soc. , 64 : 1070
   Google Scholar
• Hartmann , W. W. and Dickey , J. B. Org. Synth. Vol. , XV 6
   Google Scholar
• BEILSTEINS HANDBUCH der ORGANISCHEN CHEMIE , 6 ( 2 ) 234
   Google Scholar
• Hartmann , W. W. and Dickey , J. B. Org. Synth. Coll. Vol. , II 173
   Google Scholar
• Stenphenson , O. J. Chem. Soc. , 1954 1571
   Google Scholar