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Synthesis 2006(1): 97-102  
DOI: 10.1055/s-2005-921755
PAPER
© Georg Thieme Verlag Stuttgart · New York

A New Route to Polykis(dialkylamino)benzenes and -naphthalenes Based on Protodefluorination of Electron-Rich Fluoroaromatics: Anion Radicals of Arenes as a Simple and Effective Alternative to ‘Classical’ LAH-Based Systems

Vladimir Igorevich Sorokin*a, Valery Anatolievich Ozeryanskiia, Gennady Sergeevich Borodkinb
a Department of Organic Chemistry, Rostov State University, Zorge street 7, 344090 Rostov-on-Don, Russia
Fax: +7(863)2974156; e-Mail: vsorokin@aaanet.ru;
b Institute of Physical and Organic Chemistry, Stachki ave. 194/2, 344090 Rostov-on-Don, Russia
Further Information

Publication History

Received 14 June 2005
Publication Date:
16 December 2005 (online)

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Abstract

A simple and effective procedure for protodefluorination of electron-rich fluoroaromatic compounds has been developed. It operates with aromatic anion radicals as reducing agents and shows superior results over ‘classical’ lithium aluminum hydride based systems.

Key words

fluorinated amino arenes - aromatic anion radicals - protodefluorination - lithium aluminum hydride - electron transfer

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Stewart, J. J. P. MOPAC 6.0 Quantum Chemistry Program Exchange, University of Indiana, Bloomington, Indiana, USA.