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Acid catalyzed halogen dance on deactivated pyrroles
Author(s) -
Tutino Federico,
Papeo Gianluca,
Quartieri Francesca
Publication year - 2010
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.276
Subject(s) - chemistry , pyrrole , protonation , halogen , dance , scrambling , catalysis , ring (chemistry) , photochemistry , medicinal chemistry , organic chemistry , ion , art , linguistics , alkyl , philosophy , literature
A study on the acid catalyzed halogen dance (ACHD) on deactivated bromopyrroles is reported. A different behavior is observed when considering singly deactivated pyrrole alkylcarboxamides, or doubly deactivated pyrroleketo‐lactams (aldisines). Although less electron deficient pyrrole alkylcarboxamides suffer from ACHD, the double deactivation on keto‐lactams disfavors pyrrole ring protonation thus preventing halogen scrambling. The mechanism involved in the rearrangement is hypothesized. J. Heterocyclic Chem., 2010.