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Nucleophile Substitution von Nitrit in Nitrobenzolen, Nitrobiphenylen und Nitronaphthalinen
Author(s) -
Effenberger Franz,
Koch Markus,
Streicher Willi
Publication year - 1991
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19911240125
Subject(s) - chemistry , resorcinol , nitrobenzene , nucleophile , nitrite , nucleophilic aromatic substitution , phenols , medicinal chemistry , nucleophilic substitution , yield (engineering) , organic chemistry , nitrate , catalysis , materials science , metallurgy
Nucleophilic Substitution of Nitrite in Nitrobenzenes, Nitrobiphenyls, and Nitronaphthalenes Aromatic compounds, accessible only by multistep procedures, can be synthesized easily by nucleophilic substitution of nitrite in nitrobenzenes, nitrobiphenyls, and nitronaphthalenes. Thus, meta ‐substituted phenols 3, 4 , and 7 are obtained from 1,3‐dinitrobenzene ( 1 ) and meta ‐substituted nitrobenzenes 6 , as well as 3,5‐disubstituted phenols 10 and 5‐substituted resorcinol derivatives 11 from 3,5‐disubstituted nitrobenzenes 9 . The unsymmetrically substituted nitrobiphenyls 13, 15, 17, 19, 21, 23, 24 , and 26 are also available by nitrite exchange from the corresponding easily accessible dinitrobiphenyls 16, 18, 20, 22 , and 25 . A nitrite exchange with nucleophiles is easily possible in the 1,5‐disubstituted naphthalenes 29, 34 , while in the case of the 1,8‐disubstituted naphthalenes 31, 36 only the chloro derivative 36 undergoes this exchange under much stronger conditions in low yield.