Publication Type Journal Article
Title Lanthanide derivatives comprising arylhydrazones of beta-diketones: cooperative E/Z isomerization and catalytic activity in nitroaldol reaction
Authors Kamran T. Mahmudov M. Fátima C. Guedes da Silva Manas Sutradhar Maximilian N. Kopylovich Fatali E. Huseynov Nazim T. Shamilov Anna A. Voronina Tatyana M. Buslaeva Armando J.L. Pombeiro
Groups CCC
Journal DALTON TRANSACTIONS
Year 2015
Month
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Volume 44
Number 12
Pages 5602-5610
Abstract Two complexes [KLa(HL1)(2)\(CH3)(2)NCHO\(2)(H2O)(3)] (1) and [Sm(H2O)(9)](E-H2L2)(3)center dot 2H(2)O (2) were synthesized by the reaction of lanthanum(III) and samarium(III) nitrates with potassium 3-(2-(2,4-dioxopentan-3-ylidene) hydrazinyl)-2-hydroxy-5-nitrobenzenesulfonate (KH2L1) and potassium (E, Z)-5-chloro-3-(2-(1,3-dioxo-1-phenylbutan-2-ylidene)hydrazinyl)-2-hydrox ybenzenesulfonate (KH2L2), respectively. Both complexes were fully characterized by elemental analysis, IR, H-1 and C-13 NMR spectroscopy, ESI-MS and single-crystal X-ray diffraction. Cooperative E, Z. E isomerization of KH2L2, induced by resonance assisted hydrogen bonding and ionic interactions, occurs upon the interaction with Sm(III). Catalytic activities of KH2L1,2 and their lanthanide derivatives were evaluated in the Henry reaction of nitroethane with a variety of aromatic and aliphatic aldehydes. Good yields (up to 91\%) and diastereoselectivities (syn/anti 3 : 1) were observed in the reactions catalyzed by 1 in water.
DOI http://dx.doi.org/10.1039/c4dt03788j
ISBN
Publisher ROYAL SOC CHEMISTRY
Book Title
ISSN 1477-9226
EISSN 1477-9234
Conference Name
Bibtex ID ISI:000351439200037
Observations
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