Aromatic N-Haloazoles

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This chapter reviews chemistry of aromatic N-haloazoles, as distinct from that of N-haloamines and N-haloamides and focuses on N-haloazoles in which the halogen atom is bound to the aromatic azole ring, excluding cyclic N-haloamines, N-haloamides, and some other analogous nonaromatic systems. In some cases N-haloazoles are intermediates in the electrophilic halogenations at carbon atoms of the heteroring. This chapter illustrates that a general method for preparing N-haloazoles is the halogenation of the corresponding azoles in a neutral or anionic form with halogens or their derivatives containing a formally positively charged halogen atom. This chapter concludes that in a variety of complex reaction pathways, N-haloazoles are intermediates for C-halo derivatives and the intermediate N-haloazoles are often difficult to isolate or even detect..

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