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Characterization of a chiral menthyldimethyltin molybdate and its use as an olefin epoxidation catalyst

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Abstract

Vibrational spectroscopy and EXAFS studies of an organotin molybdate with the formula [((Me)2(menthyl)Sn)2MoO4(H2O)3.5] reveal that the compound is polymeric and contains [MoO4]2− tetrahedra coordinated to [R3Sn]+ cationic spacers. The compound can be used as a recyclable solid catalyst for the selective epoxidation of cyclooctene by tert-butylhydroperoxide. In the epoxidation of prochiral olefins such as trans-β-methylstyrene, the corresponding epoxide isomers are obtained with fairly good to excellent selectivity, albeit with low enantiomeric or diastereomeric excesses.

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Acknowledgments

The authors are grateful to the FCT, OE and FEDER for funding (Project POCI/CTM/58507/2004). We acknowledge the European Synchrotron Radiation Facility for provision of synchrotron radiation facilities and we would like to thank Silvia Ramos for assistance in using beamline BM29.

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Authors and Affiliations

  1. Instituto de Tecnologia Química e Biológica da Universidade Nova de Lisboa, Av. da Republica, Estação Agronómica Nacional, 2780-157, Oeiras, Portugal

    Marta Abrantes & Carlos C. Romão

  2. Department of Chemistry, CICECO, University of Aveiro, Campus de Santiago, 3810-193, Aveiro, Portugal

    Anabela A. Valente, Martyn Pillinger & Isabel S. Gonçalves

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  1. Marta Abrantes
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  2. Anabela A. Valente
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  3. Martyn Pillinger
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  4. Carlos C. Romão
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  5. Isabel S. Gonçalves
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Correspondence to Isabel S. Gonçalves.

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Abrantes, M., Valente, A.A., Pillinger, M. et al. Characterization of a chiral menthyldimethyltin molybdate and its use as an olefin epoxidation catalyst. Catal Lett 114, 103–109 (2007). https://doi.org/10.1007/s10562-007-9048-2

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  • DOI: https://doi.org/10.1007/s10562-007-9048-2

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