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Molecules 2016, 21(10), 1408; doi:10.3390/molecules21101408

Original Synthesis of Fluorenyl Alcohol Derivatives by Reductive Dehalogenation Initiated by TDAE

Aix-Marseille Université, CNRS, Institut de Chimie Radicalaire ICR, UMR 7273, Laboratoire de Pharmaco-Chimie Radicalaire, Marseille 13385, France
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Academic Editor: Derek J. McPhee
Received: 19 September 2016 / Revised: 18 October 2016 / Accepted: 19 October 2016 / Published: 24 October 2016
(This article belongs to the Section Organic Synthesis)
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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. View Full-Text
Keywords: tetrakis(dimethylamino)ethylene; reductive dehalogenation; single electron transfer tetrakis(dimethylamino)ethylene; reductive dehalogenation; single electron transfer
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Giuglio-Tonolo, A.G.; Terme, T.; Vanelle, P. Original Synthesis of Fluorenyl Alcohol Derivatives by Reductive Dehalogenation Initiated by TDAE. Molecules 2016, 21, 1408.

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