Add time:07/31/2019         Source:sciencedirect.com

Publisher SummaryAzodicarbonyl compounds contain a carbonyl function on both sides of the azo bond, in contrast to aliphatic and aromatic azo compounds, possess a highly reactive N=N group. Reactions in which one or both, of the nitrogen atoms of the azo group are retained in the final heterocyclic product are considered, and are classified according to the size of the new ring formed. Other reactions of azodicarbonyl (ADC) compounds, which do not give heterocyclic products, are briefly discussed. Acyclic ADC compounds, which are more correctly named as derivatives of diazene, are generally prepared from hydrazine derivatives. Cyclic ADC compounds are prepared by the oxidation of the corresponding cyclic hydrazine derivatives. The most important aspect of ADC compounds, as far as heterocyclic synthesis is concerned, is the great reactivity of the N=N bond in cycloaddition reactions with dienes, monoenes and 1,3-dipoles, and as an electrophile. Five-membered ring heterocycles can be the result of cycloaddition reactions of ADC compounds acting as 2π components with 1,3-dipoles, or as 4π components in cheletropic reactions. Other major uses of ADC compounds which do not give heterocyclic products are summarized briefly.

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