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, Sanjit Nayak, José Sánchez Costa, Arturo Robertazzi, Roberta Pievo, Ilpo Mutikainen, Olivier Roubeau, Simon J. Teat, Patrick Gamez^*, Jan Reedijk^*

^*Corresponding author for this work

School of Civil, Aerospace and Design Engineering

Research output: Contribution to journal › Article (Academic Journal) › peer-review

10 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1361-1365
Number of pages	5
Journal	Dalton Transactions
Volume	39
Issue number	5
Early online date	4 Dec 2009
DOIs	https://doi.org/10.1039/b917410a
Publication status	Published - 7 Feb 2010

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@article{d3a808fd93944e17a0935db305003fd2,

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

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.",

author = "Jinkui Tang and Sanjit Nayak and Costa, \{Jos{\'e} S{\'a}nchez\} and Arturo Robertazzi and Roberta Pievo and Ilpo Mutikainen and Olivier Roubeau and Teat, \{Simon J.\} and Patrick Gamez and Jan Reedijk",

year = "2010",

month = feb,

day = "7",

doi = "10.1039/b917410a",

language = "English",

volume = "39",

pages = "1361--1365",

journal = "Dalton Transactions",

issn = "1477-9226",

publisher = "Royal Society of Chemistry",

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TY - JOUR

T1 - Manganese(III)-mediated cyclodimerization of a hydrazinyl derivative generating an unprecedented 1,2,3,5,6-substituted leuco-verdazyl ring

AU - Tang, Jinkui

AU - Nayak, Sanjit

AU - Costa, José Sánchez

AU - Robertazzi, Arturo

AU - Pievo, Roberta

AU - Mutikainen, Ilpo

AU - Roubeau, Olivier

AU - Teat, Simon J.

AU - Gamez, Patrick

AU - Reedijk, Jan

PY - 2010/2/7

Y1 - 2010/2/7

N2 - 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.

AB - 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.

U2 - 10.1039/b917410a

DO - 10.1039/b917410a

M3 - Article (Academic Journal)

SN - 1477-9226

VL - 39

SP - 1361

EP - 1365

JO - Dalton Transactions

JF - Dalton Transactions

IS - 5

ER -

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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