Journal of Organic Chemistry p. 1008 - 1010 (1982)
Update date:2022-08-25
Topics:
Rosa, Michael De
N-Chloropyrrole (2) was formed in 65-72percent yield when pyrrole (1) in CCl4 was chlorinated with aqueous NaOCl.This intermediate rearranged in methanol to give chloropyrroles by two distinct reactions: a thermal rearrangement which gave 2-chloropyrrole (3) and an acid-catalyzed intermolecular reaction which gave 2-chloropyrrole (3), 3-chloropyrrole (4), and 2,5-dichloropyrrole (5).Nucleophilic attack on the N-Cl bond of 2 was demonstrated by reactions in the presence of CN- and SCN-.In the latter case, 2-(thiocyano)pyrrole was formed.
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