- Nucleophilic substitutions and radical reactions of phenylazocarboxylates
-
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.
- Jasch, Hannelore,Hoefling, Sarah B.,Heinrich, Markus R.
-
p. 1520 - 1532
(2012/03/11)
-
- 4-substituted tert-butyl phenylazocarboxylates-synthetic equivalents for the para-phenyl radical cation
-
First electrophile, then radical: 4-Substituted tert-butyl phenylazocarboxylates 1 are versatile synthetic equivalents of the para-phenyl radical cation 2. The tert-butyloxycarbonylazo group enables nucleophilic substitutions to proceed under mild conditions and can later be employed for the generation of aryl radicals. Copyright
- Hoefling, Sarah B.,Bartuschat, Amelie L.,Heinrich, Markus R.
-
supporting information; experimental part
p. 9769 - 9772
(2011/02/22)
-