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 carbon...

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Bibliographic Details
Published in:	Journal of organic chemistry 2012-02, Vol.77 (3), p.1520-1532
Main Authors:	Jasch, Hannelore, Höfling, Sarah B, Heinrich, Markus R
Format:	Article
Language:	eng
Subjects:	Aliphatic compounds Azo Compounds - chemistry Carboxylic Acids - chemistry Chemistry Chemistry Techniques, Synthetic Exact sciences and technology Free Radicals - chemistry Noncondensed benzenic compounds Organic chemistry Preparations and properties Reactivity and mechanisms Temperature
Online Access:	Get full text
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Summary:	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.
ISSN:	0022-3263 1520-6904