128924-06-1Relevant articles and documents
Nucleophilic substitutions and radical reactions of phenylazocarboxylates
Jasch, Hannelore,Hoefling, Sarah B.,Heinrich, Markus R.
, p. 1520 - 1532 (2012)
tert-Butyl phenylazocarboxylates are versatile building blocks for synthetic organic chemistry. Nucleophilic substitutions of the benzene ring proceed with aromatic amines and alcohols under mild conditions. The attack of aliphatic amines may be directed to the aromatic core as well as to the carbonyl unit leading to azocarboxamides. The benzene ring can further be modified through radical reactions, in which the tert-butyloxycarbonylazo group enables the generation of aryl radicals at either elevated temperatures or under acidic conditions. Radical reactions include oxygenation, halogenation, carbohalogenation, carbohydroxylation, and aryl-aryl coupling.
Nucleophilic Substitution of Nitrite in Nitrobenzenes, Nitrobiphenyls and Nitronaphthalenes
Effenberger, Franz,Koch, Markus,Streicher, Willi
, p. 163 - 173 (2007/10/02)
Aromatic compounds, accessible only by multistep procedures, can be synthesized easily by nucleophilic substitution of nitrite in nitrobenzenes, nitrobiphenyls, and nitronaphthalines.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, 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.
