@article{6f2f3559b3a54a04a27fa667fe18134b,
title = "Stepwise construction of a 4-hydroxyphenyl functionalized O,N,N-tridentate ferrocene-containing enaminone: Spectral, analytical and structural studies",
abstract = "Tetrahydropyranylation of methyl-4-hydroxybenzoate proceeds with formation of its corresponding THP aromatic ether THP-O-p-C6H 4CO2CH3 (1; THP = tetrahydropyranyl, C 5H9O). Reaction with in situ generated carbanion of acetylferrocene gave the protected organometallic complex Fc-C(O)CHC(OH)(p- C6H4-O-THP) (2, Fc(η5-C5H 5)Fe(η5-C5H4)) featuring keto-enol functionality; subsequent acidic treatment of 2 afforded the 4-hydroxyphenyl substituted counterpart Fc-C(O)CHC(OH)(p-C6H 4OH) (3) that exists as a 73/27 mixture of keto-enol/β-diketone tautomers in DMSO solution. The functionalized tridentate metalloligand Fc-C(O)CHC(p-C6H4OH)N(H)CH2CH 2NH2 (4) incorporating O,N,N-donors is readily obtained upon Schiff base condensation of 3 with 1,2-diaminoethane. Complex 4 exists exclusively as its ferrocenyl-enaminone tautomer in solution and in the solid state. Compounds 1-4 were characterized by NMR (1H, 13C) and IR spectroscopy as well as by elemental analysis and single-crystal X-ray diffraction.",
keywords = "Enaminone, Ferrocene, Metalloligand, O,N,N ligand, Tridentate ligand, X-ray structure",
author = "Salvador Celedon and Mauricio Fuentealba and Thierry Roisnel and Hamon, {Jean Ren{\'e}} and David Carrillo and Carolina Manzur",
note = "Funding Information: The authors thank Drs S. Sinbandhit and P. Jehan (CRMPO, Rennes) for assistance with NMR experiments and for recording mass spectrum of 4 , respectively. This research has been performed as part of the Chilean-French International Associated Laboratory for {\textquoteleft}{\textquoteright}Inorganic Functional Materials{\textquoteright}{\textquoteright} (LIAMIF-CNRS N°836). Financial support from the Fondo Nacional de Desarrollo Cient{\'i}fico y Tecnol{\'o}gico [FONDECYT (Chile) , Grant No. 1090310 (C.M., D.C. and M.F.)], the Vicerrector{\'i}a de Investigaci{\'o}n y Estudios Avanzados, Pontificia Universidad Cat{\'o}lica de Valpara{\'i}so, Chile (C.M. and D.C.), the CNRS and the Universit{\'e} de Rennes 1 is gratefully acknowledged. M.F. thank the BECASCHILE Program (Chile) for support of a postdoctoral fellowship. S.C. thank the CONICYT (Chile) for support of a graduate fellowship. ",
year = "2012",
month = jul,
day = "15",
doi = "10.1016/j.ica.2012.04.028",
language = "English",
volume = "390",
pages = "184--189",
journal = "Inorganica Chimica Acta",
issn = "0020-1693",
publisher = "Elsevier BV",
}