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Evidence for an indirect halogen exchange in the reaction of trans ‐ 2,3‐dibromo‐2,3‐dihydrobenzofuran with chloride ions
Author(s) -
Baciocchi Enrico,
Clementi Sergio,
Ruzziconi Renzo,
Sebastiani Giovanni V.
Publication year - 1977
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570140548
Subject(s) - chemistry , acetonitrile , halogen , chloride , nucleophile , bromide , medicinal chemistry , ion , inorganic chemistry , organic chemistry , catalysis , alkyl
Treatment of the title compound with chloride ions in acetonitrile leads mainly to the formation of trans ‐2,3‐dichloro‐2,3‐dihydrobenzofuran. Since a nucleophilic displacement of bromide anion by chloride anion can be excluded, a mechanism involving the equilibrium 2Cl − + Br 2 ⇋ 2Br − + Cl 2 is suggested.