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  • 1. Bastos, Erick L.
    et al.
    Farahani, Pooria
    Departamento de Química Fundamental, Instituto de Química, Universidade de São Paulo, São Paulo, SP, Brazil.
    Bechara, Etelvino J. H.
    Baader, Wilhelm J.
    Four‐membered cyclic peroxides: Carriers of chemical energy2017Inngår i: Journal of Physical Organic Chemistry, ISSN 0894-3230, E-ISSN 1099-1395, Vol. 30, nr 9, artikkel-id e3725Artikkel, forskningsoversikt (Fagfellevurdert)
    Abstract [en]

    Four‐membered cyclic peroxides are high‐energy compounds often associated tocold light emission, but whose chemical and biological roles are still matters ofdebate. The often‐dangerous synthesis of 1,2‐dioxetanes, achieved around 50 yearsago, has been mastered over the years to a point where some derivatives are commerciallyavailable. This fact does not imply that 1,2‐dioxetanes can be convenientlyprepared in the gram scale or that the synthesis of analogous 1,2‐dioxetanones andthe elusive 1,2‐dioxetanedione are simple. Important questions on the mechanism ofchemiluminescence and bioluminescence reactions are under experimental and theoreticalscrutiny. The available data have contributed to relate structural and mediumeffects to the quantum efficiency of these compounds to produce excited states.Consequently, such peroxides have been suggested to produce biologically relevantelectronically excited species in vivo in the absence of light. The connection of thishypothesis with melanin‐mediated photodamage in the dark has renewed the interestin such cyclic peroxides. This reviewgives some insight on the synthesis, chemiluminescencemechanism, and biological relevance of 1,2‐dioxetanes, 1,2‐dioxetanones,and 1,2‐dioxetanedione and provides practical protocols for those interested inengaging this field.

  • 2. Bondarchuk, Sergey V.
    et al.
    Smalius, Victor V.
    Minaev, Boris F.
    KTH, Skolan för bioteknologi (BIO), Teoretisk kemi och biologi. Bogdan Khmelnitsky Cherkasy National University, Ukraine .
    A combined experimental and density functional study of 1-(arylsulfonyl)-2-R-4-chloro-2-butenes reactivity towards the allylic chlorine2015Inngår i: Journal of Physical Organic Chemistry, ISSN 0894-3230, E-ISSN 1099-1395, Vol. 28, nr 6, s. 403-413Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Nucleophilic substitution and dehydrochlorination reactions of a number of the ring-substituted 1-(arylsulfonyl)-2-R-4-chloro-2-butenes are studied both experimentally and theoretically. The developed synthetic procedures are characterized by a general rapidity, cheapness, and simplicity providing moderate to high yields of 1-arylsulfonyl 1,3-butadienes (48-95%), 1-(arylsulfonyl)-2-R-4-(N,N-dialkylamino)-2-butenes (31-53%), 1-(arylsulfonyl)-2-R-2-buten-4-ols (37-61%), and bis[4-(arylsulfonyl)-3-R-but-2-enyl]sulfides (40-70%). The density functional theory B3LYP/6-311++G(2d,2p) calculations of the intermediate allylic cations in acetone revealed their high stability occurring from a resonance stabilization and hyperconjugation by the SO2Ar group. The reactivity parameters estimated at the bond critical points of the diene/allylic moiety display a high correlation (R-2>0.97) with the Hammett (sigma(p)) constants. 1-Arylsulfonyl 1,3-butadienes are characterized by a partly broken conjugated system, which follows from analysis of the two-centered delocalization () and localization () index values. The highest occupied molecular orbital energies of 1-arylsulfonyl 1,3-butadienes are lower than those of 1,3-butadiene explaining their low reactivity towards the Diels-Alder condensation.

  • 3. Jiang, Xiao
    et al.
    Yang, Xichuan
    Zhao, Changzhi
    Sun, Licheng
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Electrogenerated chemiluminescence, of benzo 15-crown-5 derivatives2009Inngår i: Journal of Physical Organic Chemistry, ISSN 0894-3230, E-ISSN 1099-1395, Vol. 22, nr 1, s. 1-8Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Novel electrogenerated chemiluminescence (ECL) reagents C1, C2, and C3 with high fluorescence quantum yields bearing 15-crown-5 moiety have been synthesized and characterized. The photophysical, electrochemical, and ECL characters of these compounds have been studied in a 1:1 (v/v) PhH/MeCN mixed solvent. The ECL intensity is enhanced distinctly with the increase in the fluorescence quantum yield. Their ECL behaviors have been studied using annihilation and co-reactant methods (tri-n-propylamine (TPrA) was used as a co-reactant), respectively. The stable ECL emissions of compounds C1-C3 can be ascribed to the typical and simple monomer ECL emission via S-route.

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