Oxidation-Proof Microemulsions: Microstructure and Reactivity in the Presence of Dioxiranes (Articolo in rivista)

Type
Label
  • Oxidation-Proof Microemulsions: Microstructure and Reactivity in the Presence of Dioxiranes (Articolo in rivista) (literal)
Anno
  • 2013-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1016/j.jcis.2013.07.034 (literal)
Alternative label
  • Annese C.; D,Accolti, L.; Fusco, C.; Mele, G.; Giorgio, G.; Colafemmina, G.; Murgia, S.; Palazzo, G. (2013)
    Oxidation-Proof Microemulsions: Microstructure and Reactivity in the Presence of Dioxiranes
    in Journal of colloid and interface science (Print); Elsevier Inc., San Diego (Stati Uniti d'America)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Annese C.; D,Accolti, L.; Fusco, C.; Mele, G.; Giorgio, G.; Colafemmina, G.; Murgia, S.; Palazzo, G. (literal)
Pagina inizio
  • 138 (literal)
Pagina fine
  • 144 (literal)
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  • http://biblioproxy.cnr.it:2052/science/article/pii/S0021979713006759 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 408 (literal)
Rivista
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  • 7 (literal)
Note
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Department of Chemistry, University of Bari \"Aldo Moro\", via Orabona 4, 70126 Bari, Italy. CNR-Istituto di Chimica dei Composti Organometallici (ICCOM), Bari Section, via Orabona 4, 70126 Bari, Italy. Department of Engineering of Innovation, I-73100 Lecce, Italy. Consorzio Interuniversitario Sistemi a Grande Interfase, CSGI. Department of Chemical & Geological Sciences, I-09042 Monserrato, CA, Italy (literal)
Titolo
  • Oxidation-Proof Microemulsions: Microstructure and Reactivity in the Presence of Dioxiranes (literal)
Abstract
  • Dioxiranes are used as reagents in a myriad of synthetically useful oxidations performed in aqueous medium. To extend such an approach also to substrates that are highly hydrophobic, we propose here the use of microemulsions based on the surfactant hexadecyltrimethylammonium hydrogen sulphate (CTAHS) because of its high stability against peroxide species. In this paper, we examine the dioxirane (isolated or generated in situ) reactivity in different CTAHS microemulsions. Yield and selectivity of the oxidation of ?-methylstyrene by dimethyldioxirane (DDO) generate \"in situ\" and of laurolactam by isolated methyl(trifluorometyl)dioxirane (TFDO) were studied. For each microemulsion, the aggregate size and the localization of the components were determined by a combination of NMR and light scattering techniques. The hydrodynamic radius of the micelles is close to the length of the surfactant and this suggests they are spherical in shape. When acetone (the precursor of DDO) is present in the formulation, it partitions itself between the aqueous bulk and the micellar palisade so that the dioxirane eventually formed is readily available to oxidize substrates secluded in the micelle. Apolar substrates, confined within the micelles, are protected from uncontrolled oxidations, leading to an astonishing high selectivity of oxidation of laurolactam to 12-nitro-lauric acid by TFDO. This opens the way to an easy procedure (performed in water under mild conditions) to synthetize ?-nitroacids. (literal)
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