- Exploring the substrate specificity of Cytochrome P450cin
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Cytochromes P450 are enzymes that catalyse the oxidation of a wide variety of compounds that range from small volatile compounds, such as monoterpenes to larger compounds like steroids. These enzymes can be modified to selectively oxidise substrates of interest, thereby making them attractive for applications in the biotechnology industry. In this study, we screened a small library of terpenes and terpenoid compounds against P450cin and two P450cin mutants, N242A and N242T, that have previously been shown to affect selectivity. Initial screening indicated that P450cin could catalyse the oxidation of most of the monoterpenes tested; however, sesquiterpenes were not substrates for this enzyme or the N242A mutant. Additionally, both P450cin mutants were found to be able to oxidise other bicyclic monoterpenes. For example, the oxidation of (R)- and (S)-camphor by N242T favoured the production of 5-endo-hydroxycamphor (65–77% of the total products, dependent on the enantiomer), which was similar to that previously observed for (R)-camphor with N242A (73%). Selectivity was also observed for both (R)- and (S)-limonene where N242A predominantly produced the cis-limonene 1,2-epoxide (80% of the products following (R)-limonene oxidation) as compared to P450cin (23% of the total products with (R)-limonene). Of the three enzymes screened, only P450cin was observed to catalyse the oxidation of the aromatic terpene p-cymene. All six possible hydroxylation products were generated from an in vivo expression system catalysing the oxidation of p-cymene and were assigned based on 1H NMR and GC-MS fragmentation patterns. Overall, these results have provided the foundation for pursuing new P450cin mutants that can selectively oxidise various monoterpenes for biocatalytic applications.
- Stok, Jeanette E.,Giang, Peter D.,Wong, Siew Hoon,De Voss, James J.
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- Towards a global greener process: from solvent-less synthesis of molybdenum(vi) ONO Schiff base complexes to catalyzed olefin epoxidation under organic-solvent-free conditions
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Nine Schiff base ligands derived from o-hydroxyaldehydes (2-hydroxybenzaldehyde, 2-hydroxy-3-methoxybenzaldehyde, 2-hydroxy- 1-naphthaldehyde) and nine corresponding dioxomolybdenum(vi) complexes, cis-[MoO2L(CH3OH)] or cis-[MoO2L(CH3OH)]·CH3OH and dinuclear [MoO2L]2, have been prepared using the conventional solution-based method as well as mechanochemically, by liquid assisted grinding (LAG). All products have been characterised by means of IR spectroscopy, thermal analyses and also by powder and five molybdenum complexes by single crystal X-ray diffraction. The crystal structure analysis of mononuclear complexes reveal distorted octahedral Mo(vi) coordination by ONO donor atoms from a dianionic tridentate Schiff base ligand, two oxido oxygen atoms from the MoO22+ moiety and an oxygen atom from the MeOH molecule trans to the oxido oxygen atom. Due to the trans effect of the oxido oxygen atom, Mo-O(MeOH) is the longest bond distance within the Mo coordination sphere and it expected to be the point of maximum reactivity of the complexes. All complexes have been studied as pre(catalysts) for the epoxidation of cis-cyclooctene, cyclohexene and (R)-limonene using aqueous tert-butyl peroxide (TBHP) as the oxidant and in the absence of an organic solvent.
- Cindri?, Marina,Pavlovi?, Gordana,Katava, Robert,Agustin, Dominique
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p. 594 - 602
(2017/02/05)
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- Activated vs. pyrolytic carbon as support matrix for chemical functionalization: Efficient heterogeneous non-heme Mn(II) catalysts for alkene oxidation with H2O2
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Two types of heterogeneous catalytic materials, MnII-L3imid@Cox and MnII-L3imid@PCox, have been synthesized and compared by covalent grafting of a catalytically active [MnII-L3imid] complex on the surface of an oxidized activated carbon (Cox) and an oxidized pyrolytic carbon from recycled-tire char (PCox). Both hybrids are non-porous bearing graphitic layers intermixed with disordered sp2/sp3 carbon units. Raman spectra show that (ID/IG)activatedcarbon > (ID/IG)pyrolyticcarbon revealing that oxidized activated carbon(Cox) is less graphitized than oxidized pyrolytic carbon (PCox). The MnII-L3imid@Cox and MnII-L3imid@PCox catalysts were evaluated for alkene oxidation with H2O2 in the presence of CH3COONH4. Both showed high selectivity towards epoxides and comparing the achieved yields and TONs, they appear equivalent. However, MnII-L3imid@PCox catalyst is kinetically faster than the MnII-L3imid@Cox (accomplishing the catalytic runs in 1.5 h vs. 5 h). Thus, despite the similarity in TONs MnII-L3imid@PCox achieved extremely higher TOFs vs. MnII-L3imid@Cox. Intriguingly, in terms of recyclability, MnII-L3imid@Cox could be reused for a 2th run showing a ~20% loss of its catalytic activity, while MnII-L3imid@PCox practically no recyclable. This phenomenon is discussed in a mechanistic context; interlinking oxidative destruction of the Mn-complex with high TOFs for MnII-L3imid@PCox, while the low-TOFs of MnII-L3imid@Cox are preventive for the oxidative destruction of the Mn-complex.
- Simaioforidou,Papastergiou,Margellou,Petrakis,Louloudi
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p. 516 - 525
(2016/12/16)
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- Efficient Epoxide Hydrolase Catalyzed Resolutions of (+)- and (-)-cis/trans-Limonene Oxides
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The synthesis of enantiomerically pure cis- and trans-limonene oxides and their corresponding diols from easily accessible raw materials has been of much interest for a long time. A straightforward one-step biocatalytic resolution of the (+)-cis/trans limonene oxide and the (-)-cis/trans-limonene oxide has been investigated. Epoxide hydrolases showing complementary stereoselectivity were recombinantly expressed in Escherichia coli, which allowed easy purification. The conditions for the selective epoxide hydrolase catalyzed ring-opening reactions have been optimized and enabled the preparation of all limonene oxide enantiomers. The described utilization of recombinant epoxide hydrolases for the synthesis of all limonene oxide enantiomers was superior to chemical routes and represents a highly resource-efficient one-step preparation.
- Ferrandi, Erica Elisa,Marchesi, Carlotta,Annovazzi, Celeste,Riva, Sergio,Monti, Daniela,Wohlgemuth, Roland
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p. 3171 - 3178
(2015/10/19)
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- Catalytic activity of molybdenum(II) complexes in homogeneous and heterogeneous conditions
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The new complexes [MoBr(η3-C3H5)(CO)2(L)2] (C1) and [MX2(CO)3(L)2] (M = Mo(II), X = I (C2); M = Mo(II), X = Br (C3); M = W(II), X = I (C4); M = W(II), X = Br (C5)) were synthesized by reaction of 2-amino-1,3,4-thiadiazole (L) with [MoBr(η3-C3H5)(CO)2(NCCH3)2] (1), [MoI2(CO)3(CH3CN)2](M = Mo (2); M = W (4)), or [MoBr2(CO)3(CH3CN)2](M = Mo (3); M = W (5)) in 2:1 ratio. The five complexes were immobilized in MCM-41, yielding the materials MCM-Cn (n = 1-5), and C1 was also immobilized in silica gel (Silica-C1) and in a polyhedral oligomeric silsesquioxane (Cube-C1). Complexes and materials were fully characterized by spectroscopic techniques and elemental analysis. DFT calculations showed that several C1 isomers should coexist. The as synthesized and supported complexes were tested as catalysts on the oxidation of geraniol, cis-hex-3-en-1-ol, trans-hex-3-en-1-ol, (S)-limonene, and 1-octene. The conversions and TOF significantly depend on the complex and the nature of the substrate. The general conclusions are (i) complex C1 has the highest activity; (ii) tungsten complexes C4 and C5 are more active than the molybdenum analogues; (iii) the immobilization of the catalysts improves the performance; and (iv) silica gel and the polyhedral oligomeric silsesquioxane supports modify the selectivity, leading to products different from the one obtained with MCM for specific substrates.
- Vasconcellos Dias, Maria,Saraiva, Marta S.,Ferreira, Paula,Calhorda, Maria José
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p. 1465 - 1478
(2015/05/13)
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- Monoterpene hydroxylation with an artificial self-sufficient P450 utilizing a P450SMO reductase domain for the electron transfer
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Cytochrome P450SMO from Rhodococcus sp. ECU0066 is a natural self-sufficient P450 monooxygenase, consisting of a heme domain, a flavin-reductase domain containing FMN and NADPH binding sites, and a [Fe2S2] ferredoxin domain. P450cam catalyzes the hydroxylation of camphor to 5-exo-hydroxycamphor. The variant P450cam (Y96F/V247L) was reported for the oxidation of monoterpene by protein engineering. In this work, we constructed an artificial self-sufficient P450-type monoterpene hydroxylase by connecting the P450SMO reductase domain and the P450cam (Y96F/V247L) domain together with a linker region (G4S)4. The resultant chimeric P450 enzyme could catalyze the hydroxylation of (-)-limonene and α-pinene as well as camphor, which were all inactive for the natural fusion protein P450SMO. Co-expression of the fused P450 with a glucose dehydrogenase (GDH) improved the (-)-limonene conversion as sufficient NADPH was regenerated in the system with glucose as a cosubstrate. This work illustrated that P450SMO reductase might act as an electron donor partner of P450s and might be used for fusion with heterogeneous P450 domains to elucidate the catalytic function of other unknown P450s.
- Luan, Zheng-Jiao,Yin, Yue-Cai,Li, Ai-Tao,Yu, Hui-Lei,Xu, Jian-He
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- Making Fe(BPBP)-catalyzed C-H and CC oxidations more affordable
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The limited availability of catalytic reaction components may represent a major hurdle for the practical application of many catalytic procedures in organic synthesis. In this work, we demonstrate that the mixture of isomeric iron complexes [Fe(OTf)2(mix-BPBP)] (mix-1), composed of Λ-α-[Fe(OTf)2(S,S-BPBP)] (S,S-1), Δ-α- [Fe(OTf)2(R,R-BPBP)] (R,R-1) and Δ/Λ-β-[Fe(OTf) 2(R,S-BPBP)] (R,S-1), is a practical catalyst for the preparative oxidation of various aliphatic compounds including model hydrocarbons and optically pure natural products using hydrogen peroxide as an oxidant. Among the species present in mix-1, S,S-1 and R,R-1 are catalytically active, act independently and represent ca. 75% of mix-1. The remaining 25% of mix-1 is represented by mesomeric R,S-1 which nominally plays a spectator role in both C-H and C=C bond oxidation reactions. Overall, this mixture of iron complexes displays the same catalytic profile as its enantiopure components that have been previously used separately in sp3 C-H oxidations. In contrast to them, mix-1 is readily available on a multi-gram scale via two high yielding steps from crude dl/meso-2,2′-bipyrrolidine. Next to its use in C-H oxidation, mix-1 is active in chemospecific epoxidation reactions, which has allowed us to develop a practical catalytic protocol for the synthesis of epoxides.
- Yazerski, Vital A.,Spannring, Peter,Gatineau, David,Woerde, Charlotte H.M.,Wieclawska, Sara M.,Lutz, Martin,Kleijn, Henk,Klein Gebbink, Robertus J.M.
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supporting information
p. 2062 - 2070
(2014/03/21)
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- Highly enantioselective olefin epoxidation controlled by helical confined environments
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Helical mesoporous materials of the MCM-41 type are important materials that can be prepared by onepot synthesis procedures with a co-surfactant. A control of the characteristics at a local level is of the most important in the view of the applications of such materials. However, there are not many studies relating such features with synthetic approaches. In this work, we prepared both helical and regular channel materials from Si-based MCM-41 type. Afterward, a bpy derivative was used as ligand to coordinate MoII/VI. The complexes and the new materials were tested as the catalytic precursors in the epoxidation of cis-cyclooctene, styrene, 1-octene, R-(+)-limonene and trans-hex-2-en-1-ol, using tert-butylhydroperoxide (TBHP) as oxidant. Although almost all the catalysts were 100% selective toward the epoxide, the conversions were in general good. The major achievement of these catalysts is an outstanding stereocontrol of the reaction products. In addition, these catalysts were found to be very effective under several circumstances. This is certainly an important contribution for such concept and may render such materials further applications where chiral recognition is important.
- Fernandes, Cristina I.,Saraiva, Marta S.,Nunes, Teresa G.,Vaz, Pedro D.,Nunes, Carla D.
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- Non-heme iron catalysis in CC, C-H, and CH2 oxidation reactions. Oxidative transformations on terpenoids catalyzed by Fe(bpmen)(OTf)2
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The oxidation of terpene olefins with hydrogen peroxide in the presence of the non-hemo catalyst 5a afforded mixtures of epoxides whose composition was dependent upon the oxidation protocol used in each case. With terpenoid enones, the mixtures obtained evolved from clean epoxidation of α-ionone 23 to the clean allylic oxidation of damascone 28 due to the progressive deactivation of the electron density on the double bonds present in this series. The oxidation of bicyclic and tricyclic terpenoids afforded oxidation products coming from epoxidation, to olefin degradation, methyne and methylene activation products. Probably, the most attractive result was the synthesis of the Magnus lactone 46, from the tricyclic ether 45, with 88% yield and 100% conversion.
- Clemente-Tejeda, David,López-Moreno, Alejandro,Bermejo, Francisco A.
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p. 2977 - 2986
(2013/03/29)
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- A simple and efficient oxidation procedure for the synthesis of acid-sensitive epoxides
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A mild and straightforward epoxidation protocol based on sodium perborate as primary oxidant and sodium dehydrocholate as organomediator under homogeneous conditions is described. In particular, geraniol, linalool, 3-carene, and a-pinene are quantitatively converted into the corresponding 6,7-epoxides and transepoxides, respectively. The bile acid salt is recovered from the reaction mixture and may be reused with unchanged efficiency and selectivity. Georg Thieme Verlag Stuttgart.
- Bortolini, Olga,Fantin, Giancarlo,Fogagnolo, Marco
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experimental part
p. 1123 - 1126
(2009/12/04)
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- CrIII(salen) catalysed asymmetric ring opening of monocyclic terpene-epoxides
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The racemic CrIII(salen) complex was found to be an efficient catalyst for the asymmetric ring opening (ARO) with TMSN3 of cyclic 1,2-epoxy-terpenes bearing C4-substituents.
- Dioos, Bart M. L.,Jacobs, Pierre A.
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p. 4715 - 4717
(2007/10/03)
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- Alumina-Catalyzed Epoxidation with Hydrogen Peroxide: Recycling Experiments and Activity of Sol-Gel Alumina
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Commercial alumina looses some activity after the first epoxidation reaction of (S)-limonene with hydrogen peroxide, but maintains a good activity and a very high selectivity in the subsequent three reactions. After this its activity is strongly reduced, probably due to structural modifications. Aluminas obtained by sol-gel methods are normally less active than the commercial alumina. However, the use of monomeric aluminum sec-butoxide and of oxalic acid to form stable alumina mesophases allows a very active alumina to be obtained, which catalyses the epoxidation of the less reactive cyclohexene with hydrogen peroxide in 98% yield. Close to 50% of the active oxygen is used up in the formation of molecular oxygen.
- Cesquini, Renato G.,De S. E Silva, Juliana M.,Woitiski, Camile B.,Mandelli, Dalmo,Rinaldi, Roberto,Schuchardt, Ulf
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p. 911 - 914
(2007/10/03)
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- Aerobic epoxidation of natural terpenes: Study of the catalytic activity of new Ru-1,2,4-triazepine compelxes
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Aerobic epoxidation of a range of natural terpenic olefines was carried out by using the triazepinic complexes [RuCl(TAZO)(p-cymene)] C1 and [Ru(TAZS)(p-cymene)]2 C2, recently prepared from [RuCl2(p-cymene)]2 and the corresponding 1,2,4-triazepines (HTAZO and H2TAZS). While, good similar stereoselectivity was observed for the two complexes, C1 was shown to be more effective and chemioselective.
- Fdil, Na?ma,Ait Itto, My Youssef,Ait Ali, Mustapha,Karim, Abdellah,Daran, Jean-Claude
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p. 8769 - 8771
(2007/10/03)
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- Substrate-induced diastereoselectivity in the dimethyldioxirane epoxidation of simple alkenes and dienes
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Various alkenes and dienes, such as (R)- or (S)-limonene 2, 2-carene 6, 3-carene 8, (R)-α-pinene 10, (S)-α-pinene 12, and endo-dicyclopentadiene 14 were transformed into the corresponding mono- and bis-epoxides by epoxidation with dimethyldioxirane (as an acetone solution). The selectivity observed in these epoxidations is explained by the assumption of hydrogen bonding between bridge protons and the dioxirane.
- Asouti,Hadjiarapoglou
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p. 1847 - 1850
(2007/10/03)
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- Resolution of limonene 1,2-epoxide diastereomers by mercury(II) ions
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When HgCl2 was added to a diastereomeric mixture of cis- and trans-(4S)-limonene 1,2-epoxide, the Hg(II) ions stereoselectively complexed to the cis epoxide, enabling ring opening by water. The resulting mercuric salt could be demetalated by treatment with NaBH4, giving a mixture of diastereomeric (1S,2S,4S)- and (1R,2R,4S)-diols. The remaining trans-(4S)-epoxide was obtained in >98% d.e. and 40% yield. For reactions on a larger scale, the most convenient reaction system was Hg(OAc)2 in 50% acetone/tris-HCl buffer pH 7.0. The reaction rate was affected by the pH, with pH 6-8 as optimum.
- Van der Werf, Mari?t J.,Jongejan, Hugo,Franssen, Maurice C.R.
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p. 5521 - 5524
(2007/10/03)
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- Engineering the haem monooxygenase cytochrome P450cam for monoterpene oxidation
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Monooxygenated terpenes are fine fragrance and flavouring chemicals, and active site mutants of the haem monooxygenase cytochrome P450cam which were designed to have improved complementarity between the substrate binding pocket and the monoterp
- Bell,Sowden,Wong
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p. 635 - 636
(2007/10/03)
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- Aerobic epoxidation of alkenes using polymer-bound Mukaiyama catalysts
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Nickel(II) acetylacetonate bound to polybenzimidazole has been shown to be an efficient catalyst for the aerobic epoxidation of alkenes with an aldehyde as co-reactant. Rates of reaction and yields of epoxide are higher with this system than with dissolved Ni(II) acetylacetonate under otherwise identical conditions. The polymer-bound complex acts as a heterogeneous catalyst and can be recovered from the reaction mixture. Some loss of activity is observed upon re-use of the catalyst due to leaching of the metal complexes.
- Wentzel, Bastienne B.,Leinonen, Salla-M.,Thomson, Stephen,Sherrington, David C.,Feiters, Martinus C.,Nolte, Roeland J.M.
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p. 3428 - 3431
(2007/10/03)
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- A mechanistic investigation of alkene epoxidation by sterically encumbered trans-dioxoruthenium(VI) porphyrins
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The highly substituted dioxoruthenium(VI) porphyrins [Ru(VI)(DPP)O2] (1a; H2DPP = 2,3,5,7,8,10,12,13,15,17,18,20-dodecaphenylporphyrin), [Ru(VI)(TDCPP)O2] (1b; H2TDCPP = meso-tetrakis(2,6- dichlorophenyl)porphyrin), and [Ru(VI)(TMOPP)O2] (1c; H2TMOPP = meso- tetrakis(2,4,6-trimethoxyphenyl)porphyrin) are competent oxidants for alkene epoxidation. The oxidations were carried out in a CH2Cl2/Hpz solution, and a paramagnetic bis(pyrazolato)ruthenium(IV) porphyrin, [Ru(IV)(Por)(pz)2] (2; H2Por = H2DPP, H2TDCPP, H2TMOPP), was isolated and characterized. For the oxidation of cis-alkenes, stereoselectivity is dependent upon both the alkenes and the ruthenium oxidants, and it decreases in the order: cis- stilbene > cis-β-methylstyrene > cis-β-deuteriostyrene. The observation of inverse secondary KIE for the oxidation of β-d2-styrene [k(H)/k(D) = 0.87 (1a); 0.86 (1b)] but not for the α-deuteriostyrene oxidations suggests that the C-O bond formation is more advanced at the C(β) atom than at the C(α) atom of styrene, consistent with a nonconcerted mechanism. By consideration of spin delocalization and polar effects, the second-order rate constants for the oxidation of para-substituted styrenes by complexes 1a-c can linearly correlate with the carboradical substituent constants σ(mb) and σ(JJ)· (Jiang, X.-K. Acc. Chem. Res. 1997, 30, 283). This implies that the styrene oxidation by the dioxoruthenium(VI) porphyrins should involve rate-limiting generation of a benzylic radical intermediate, and the magnitude of |ρ·(JJ)/ρ(mb)| > 1 suggests that the spin delocalization effect is more important than the polar effect in the epoxidation reactions. The spontaneous epoxidation of trans-β-methylstyrene by the sterically encumbered [Ru(VI)(TDCPP)O2] and [Ru(VI)(TMOPP)O2] complexes and the comparable ΔS((+)) values for their reactions with trans-β-methylstyrene and styrene are incompatible with the 'side-on approach' model; a 'head-on approach' model is implicated.
- Liu, Chun-Jin,Yu, Wing-Yiu,Che, Chi-Ming,Yeung, Chi-Hung
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p. 7365 - 7374
(2007/10/03)
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- Ruthenium meso-tetrakis(2,6-dichlorophenyl)porphyrin complex immobilized in mesoporous MCM-41 as a heterogeneous catalyst for selective alkene epoxidations
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A ruthenium complex of meso-tetrakis(2,6-dichlorophenyl)porphyrin, [RuII(TDCPP)(CO)(EtOH)], is immobilized into mesoporous MCM-41 molecular sieves; the supported Ru catalyst can effect highly selective heterogeneous alkene epoxidations using 2,6-dichloropyridine TV-oxide as terminal oxidant. Aromatic and aliphatic alkenes can be efficiently converted to their epoxides in good yields and selectivities, and cis-alkenes such as czs-stilbene, cis-β-methylstyrene, and cis-β-deuteriostyrene are epoxidized stereospecifically. Oxidation of cycloalkenes, e.g., norbornene and cyclooctene, can be carried out effectively using the heterogeneous Ru-catalyzed reaction while these alkenes are unreactive in the zeolite-based titanium silicate (TS-l)-catalyzed conditions (Murugavel, R.; Roesky, H. W. Angew. Chem., Int. Ed. Engl. 1997, 36, 477). On the other hand, the Ru/M-41(m) catalyst displays size selectivity in the (+)-limonene oxidation where the terminal C=C bond (vs internal trisubstituted C=C bond) becomes more readily oxidized. Bulky 3,4,6-tri-O-benzyl-D-glucal has failed to react under the heterogeneous Ru-catalyzed conditions, whereas the smaller acetyl derivative is converted to a 3:1 mixture of α- and β-glycal epoxides. The Ru/M-41(m) catalyst can be used repeatedly, and 67% of its initial activity is retained after 11 691 turnovers (three runs). The loss of activity is attributed to catalyst leaching and/or deactivation. On the basis of Hammett correlation (ρ+ = -0.72, R = 0.997) and product studies (cyclohexene and crs-alkenes as the substrates), a reactive dioxorutheniumCVI) porphyrin intermediate is not favored. An oxoruthenium(V) complex or oxoruthenium(IV) porphyrin cation radical could be the key intermediate for this highly selective epoxidation reaction.
- Liu, Chun-Jing,Yu, Wing-Yiu,Li, Shou-Gui,Che, Chi-Ming
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p. 7364 - 7369
(2007/10/03)
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- HYDROGENOLYSE EN PHASE LIQUIDE SUR Pd/C DES EPOXYDES DU CARVOMENTHENE ET DU LIMONENE
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Hydrogenolysis over Pd/C of cis and trans epoxides of carvomenthene and limonene give a mixture of hydrocarbons, secondary and tertiary alcohols, and ketones in proportions dependent upon the nature of the starting material.In the limonene epoxides, the extracyclic double bond plays an important role in the opening of the oxirane ring through a common unsaturated tertiary alcohol intermediate by double bond migration, hydrogenation of which leads to the products.For the carvomenthene epoxides the results are similar to those found in the 4-t-butyl series with competition between cis addition and trans addition of hydrogen.The presence of the isopropenyl group leads to slower reaction rates in comparison with t-butyl analogues.
- Accrombessi, G.,Geneste, P.,Olive, J.-L.,Pavia, A. A.
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p. 3135 - 3140
(2007/10/02)
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- Stereoselective Cyclization assisted by the Selenyl Group. Biogenetic-type Synthesis in the p-Menthane Series
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Acid-catalysed cyclization of the β-hydroxyselenide (3), derived from linalyl acetate (1), afforded the trans-p-menthanes (4) and (5), the structures of which were confirmed by their transformation into (6), (11), (8), and (13), and alternative syntheses of these compounds.The structure determination of some products obtained by the reaction of limonene and α-terpineol epoxides with phenylselenium anion was also carried out.
- Kametani, Tetsuji,Kurobe, Hiroshi,Nemoto, Hideo
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p. 756 - 760
(2007/10/02)
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