Chlorination of Pyrrole. N-Chloropyrrole

Formation and Rearrangement to 2- and 3-Chloropyrrole

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

N-Chloropyrrole (2) was formed in 65–72% 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 intermodular 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.

Original languageEnglish (US)
Pages (from-to)1008-1010
Number of pages3
JournalJournal of Organic Chemistry
Volume47
Issue number6
DOIs
StatePublished - Jan 1 1982

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Pyrroles
Chlorination
Methanol
Acids
Hot Temperature

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

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title = "Chlorination of Pyrrole. N-Chloropyrrole: Formation and Rearrangement to 2- and 3-Chloropyrrole",
abstract = "N-Chloropyrrole (2) was formed in 65–72{\%} 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 intermodular 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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Chlorination of Pyrrole. N-Chloropyrrole : Formation and Rearrangement to 2- and 3-Chloropyrrole. / De Rosa, Michael.

In: Journal of Organic Chemistry, Vol. 47, No. 6, 01.01.1982, p. 1008-1010.

Research output: Contribution to journalArticle

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N2 - N-Chloropyrrole (2) was formed in 65–72% 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 intermodular 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.

AB - N-Chloropyrrole (2) was formed in 65–72% 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 intermodular 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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