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Synthesis 2006(1): 146-150  
DOI: 10.1055/s-2005-921745
PAPER
© Georg Thieme Verlag Stuttgart · New York

Unusually Facile Syntheses of Diquat (6,7-Dihydrodipyrido[1,2-a:2′,1′-c]pyrazinediium) and Related Cations

Benjamin J. Coe*, Naomi R. M. Curati, Emma C. Fitzgerald
School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, UK
Fax: +44(161)2754598; e-Mail: b.coe@man.ac.uk;
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Publication History

Received 15 June 2005
Publication Date:
16 December 2005 (online)

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Abstract

A new and versatile method for the synthesis of cyclic diquaternary cations under mild conditions is described. Treatment of various α-diimines with 1,2-bis(triflyloxy)ethane in diethyl ether, chloroform, or dichloromethane at room temperature affords diquats in yields of up to 98%.

Key words

cations - heterocycles - polycycles - diquats - bis(triflyl­oxy)ethane