title: Original Synthesis of Fluorenyl Alcohol Derivatives by Reductive Dehalogenation Initiated by TDAE.
abstract: We report here a novel and easy-to-handle reductive dehalogenation of 9-bromofluorene in the presence of arylaldehydes and dicarbonyl derivatives to give the corresponding fluorenyl alcohol derivatives and Darzens epoxides as by-products in tetrakis(dimethylamino)ethylene (TDAE) reaction conditions. The reaction is believed to proceed via two successive single electron transfers to generate the fluorenyl anion which was able to react with different electrophiles. A mechanistic study was conducted to understand the formation of the epoxide derivatives.
authors: Aix-Marseille Université, CNRS, Institut de Chimie Radicalaire ICR, UMR 7273, Laboratoire de Pharmaco-Chimie Radicalaire, Marseille 13385, France. gamal.giuglio-tonolo@univ-amu.fr.
authors: Alain Gamal
authors: AG
authors: Giuglio-Tonolo
authors: Aix-Marseille Université, CNRS, Institut de Chimie Radicalaire ICR, UMR 7273, Laboratoire de Pharmaco-Chimie Radicalaire, Marseille 13385, France. thierry.terme@univ-amu.fr.
authors: Thierry
authors: T
authors: Terme
authors: Aix-Marseille Université, CNRS, Institut de Chimie Radicalaire ICR, UMR 7273, Laboratoire de Pharmaco-Chimie Radicalaire, Marseille 13385, France. patrice.vanelle@univ-amu.fr.
authors: Patrice
authors: P
authors: Vanelle
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry; D004123:Dimethylamines / Q000737:chemistry*; D004983:Ethanolamines / Q000138:chemical synthesis*; D005030:Ethylenes / Q000737:chemistry*; D005449:Fluorenes / Q000138:chemical synthesis* / Q000737:chemistry; D000078102:Lumefantrine; D011422:Propionates / Q000737:chemistry
chemical_list: C000618776:9-fluorenylidene; D000438:Alcohols; D000894:Anti-Inflammatory Agents, Non-Steroidal; D004123:Dimethylamines; D004983:Ethanolamines; D005030:Ethylenes; D005449:Fluorenes; D011422:Propionates; C025618:cicloprofen; D000078102:Lumefantrine; C548965:tetrakis(dimethylamino)ethylene
keywords: reductive dehalogenation; single electron transfer; tetrakis(dimethylamino)ethylene