title: Nucleophilic substitutions and radical reactions of phenylazocarboxylates.
abstract: 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.
authors.affiliation: Department of Chemistry and Pharmacy, Pharmaceutical Chemistry, Friedrich-Alexander-Universität Erlangen-Nürnberg, Schuhstraße 19, 91052 Erlangen, Germany.
authors.forename: Hannelore
authors.initials: H
authors.lastname: Jasch
authors.forename: Sarah B
authors.initials: SB
authors.lastname: Höfling
authors.forename: Markus R
authors.initials: MR
authors.lastname: Heinrich
mesh_terms: D001391:Azo Compounds / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D005609:Free Radicals / Q000737:chemistry; D013696:Temperature
chemical_list: D001391:Azo Compounds; D002264:Carboxylic Acids; D005609:Free Radicals