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Issue 5, 2010
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Manganese(iii)-mediated cyclodimerization of a hydrazinyl derivative generating an unprecedented 1,2,3,5,6-substituted leuco-verdazyl ring

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Abstract

The one-pot reaction of Mn(OAc)3 with two equivalents of 6-(pyridine-2-ylhydrazonomethyl)phenol (Hphp) in methanol leads to a unique leuco-verdazyl-type ring. The remarkable cyclodimerization reaction is proposed to involve a number of one-electron oxidative steps mediated by Mn3+ ions, as well as a very uncommon 1,2-radical aryl migration and a nucleophilic attack of the solvent, i.e. methanol.

Graphical abstract: Manganese(iii)-mediated cyclodimerization of a hydrazinyl derivative generating an unprecedented 1,2,3,5,6-substituted leuco-verdazyl ring

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Article information


Submitted
24 Aug 2009
Accepted
05 Nov 2009
First published
04 Dec 2009

Dalton Trans., 2010,39, 1361-1365
Article type
Paper

Manganese(III)-mediated cyclodimerization of a hydrazinyl derivative generating an unprecedented 1,2,3,5,6-substituted leuco-verdazyl ring

J. Tang, S. Nayak, J. S. Costa, A. Robertazzi, R. Pievo, I. Mutikainen, O. Roubeau, S. J. Teat, P. Gamez and J. Reedijk, Dalton Trans., 2010, 39, 1361
DOI: 10.1039/B917410A

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