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

Jinkui Tang; Sanjit Nayak; José Sánchez Costa; Arturo Robertazzi; Roberta Pievo; Ilpo Mutikainen; Olivier Roubeau; Simon J. Teat; Patrick Gamez; Jan Reedijk

doi:10.1039/B917410A

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

Jinkui Tang,^b Sanjit Nayak,^a José Sánchez Costa,^c Arturo Robertazzi,^d Roberta Pievo,^a Ilpo Mutikainen,^e Olivier Roubeau,^f Simon J. Teat,^g Patrick Gamez*^a and Jan Reedijk*^a

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* Corresponding authors

^a Leiden Institute of Chemistry, Gorlaeus Laboratories, Leiden University, P.O. Box 9502, Leiden, The Netherlands
E-mail: p.gamez@chem.leidenuniv.nl
Fax: 31 715274671

^b State Key Laboratory of Rare Earth Resource Utilization, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. China

^c Departament de Química Inorgànica, Universitat de Barcelona, Diagonal, 647, Spain

^d CNR-INFM SLACS and Dipartimento di Fisica, Università di Cagliari, S.P. Monserrato-Sestu Km 0.700, I-09042 Monserrato, Italy

^e Department of Chemistry, Laboratory of Inorganic Chemistry, University of Helsinki, P.O. Box 55 (A.I. Virtasenaukio 1), Helsinki, Finland

^f Instituto de Ciencia de Materiales de Aragón, CSIC and Universidad de Zaragoza, Plaza San Francisco, s/n, 50009 Zaragoza, Spain

^g Advanced Light Source, Lawrence Berkeley National Laboratory, Berkeley, California 94720, USA

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.

Dalton Transactions

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

Abstract

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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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