title: Superacid-promoted reactions of alpha-ketoamides and related systems.
abstract: The superacid-promoted reactions of alpha-hydroxy and alpha-ketoamides have been studied. Ionization of these compounds leads to varied aryl-substituted oxyindole products. In some cases, electrocyclization can lead to substituted fluorene products. Dicationic, superelectrophilic intermediates are proposed as intermediates leading to the products from alpha-hydroxy and alpha-ketoamides.
authors.affiliation: Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, Illinois 60115, USA.
authors.forename: Kiran Kumar Solingapuram
authors.initials: KK
authors.lastname: Sai
authors.forename: Pierre M
authors.initials: PM
authors.lastname: Esteves
authors.forename: Eduardo Tanoue
authors.initials: ET
authors.lastname: da Penha
authors.forename: Douglas A
authors.initials: DA
authors.lastname: Klumpp
mesh_terms: D000577:Amides / Q000737:chemistry*; D001561:Benzilates / Q000737:chemistry; D002412:Cations; D003500:Cyclization; D004563:Electrochemistry; D005449:Fluorenes / Q000737:chemistry; D006900:Hydroxylation; D007211:Indoles / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008333:Mandelic Acids / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000577:Amides; D001561:Benzilates; D002412:Cations; D005449:Fluorenes; D007211:Indoles; D007659:Ketones; D008333:Mandelic Acids; C041509:fluorene; C037938:mandelic acid