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Issue 46, 2014

Electronic effects of substituents on the stability of the iridanaphthalene compound [Ir[upper bond 1 start]Cp*{[double bond, length as m-dash]C(OMe)CH[double bond, length as m-dash]C(o-C[upper bond 1 end]6H4)(Ph)}(PMe3)]PF6

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Abstract

Iridanaphthalene complexes are synthesized from the corresponding methoxy(alkenyl)carbeneiridium compounds. The electronic character of the substituents on the 6-position of the metallanaphthalene ring is crucial from the point of view of the stability of the iridanaphthalene, [Ir[upper bond 1 start]Cp*{[double bond, length as m-dash]C(OMe)CH[double bond, length as m-dash]C(o-C[upper bond 1 end]6H4)(Ph)}(PMe3)]PF6, vs. its transformation to the corresponding indanone derivatives. Stability studies of the iridanaphthalene compounds revealed that strong electron donor substituents (–OMe) stabilize the iridanaphthalene, while weak electron donor (–Me) and electron withdrawing (–NO2) groups favor the formation of indanone derivatives. Two possible indanone isomers can be obtained in the conversion of the unstable iridanaphthalene complexes and a mechanism for the formation of these isomers is proposed.

Graphical abstract: Electronic effects of substituents on the stability of the iridanaphthalene compound [Ir [[upper bond 1 start]] Cp*{ [[double bond, length as m-dash]] C(OMe)CH [[double bond, length as m-dash]] C(o-C [[upper bond 1 end]] 6H4)(Ph)}(PMe3)]PF6

Supplementary files

Article information


Submitted
09 Sep 2014
Accepted
04 Oct 2014
First published
06 Oct 2014

Dalton Trans., 2014,43, 17366-17374
Article type
Paper
Author version available

Electronic effects of substituents on the stability of the iridanaphthalene compound [Ir[upper bond 1 start]Cp*{[double bond, length as m-dash]C(OMe)CH[double bond, length as m-dash]C(o-C[upper bond 1 end]6H4)(Ph)}(PMe3)]PF6

M. Talavera, J. Bravo, J. Castro, S. García-Fontán, J. M. Hermida-Ramón and S. Bolaño, Dalton Trans., 2014, 43, 17366 DOI: 10.1039/C4DT02744B

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