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Santelli, Maurice.

ACL - Articles dans des revues à comité de lecture

32 références.
2019

  • Audran, G.; Marque, S. R. A.; Santelli, M. Journal of Physical Chemistry A 2019, 123 (7), 1380-1388.
    Résumé : After quantum calculations of absolute free energies of polyatomic sulfur derivatives or hydrocarbon oligomer compounds, we have studied the variations of G(n) as a function of the number of repeating units n (sulfur atoms or hydrocarbon units, G(n) = 2 to about 60), and observed that these values can be correlated by (a) a nearly perfect linear relationship, Gn = An + B (A and B, constants), with a high accuracy which enables an extrapolation for higher values of n, and (b) a power law:, delta G = G(n)/n - G((n-1)) /(n-1) = C/n(d) (C and d, constants). From comparison of variations of the C-C bond lengths, we show that the conjugation of trans-polyenes (up to C60H62) is more important than for polyynes (up to C60H2).
2018

  • Audran, G.; Marque, S. R. A.; Santelli, M. Tetrahedron 2018, 74 (43), 6221-6261.
    Résumé : Various aspects of the structure, the reactivity in organic synthesis, in the atmosphere, in environment, in biology of ozone are described. Emphasis is placed on the relation with singlet oxygen and dihydrotrioxide. (C) 2018 Elsevier Ltd. All rights reserved.

  • Audran, G.; Marque, S. R. A.; Siri, D.; Santelli, M. Chemistryselect 2018, 3 (31), 9113-9120.
    Résumé : Heats of combustion of n-alkanes, Delta H-n , from CH4 to C60H122 have been determined using quantum-chemical calculations. We have observed a nearly perfect linear relationship between Delta H-n(theo) and the experimental values of heats of combustion for methane to n-eicosane. Then, we were able to extrapolate for 21 <= n <= 60. Interestingly, we showed that the variations of the increments H[n-CnH(2n+2)]/n -H [n-C((n-1))H-2n]/(n-1) against n led to a characteristic power law distribution.
2017

  • Audran, G.; Adiche, C.; Bremond, P.; El Abed, D.; Hamadouche, M.; Siri, D.; Santelli, M. Tetrahedron Letters 2017, 58 (10), 945–948.
    Résumé : Enamines derived from cyclic ketones react with arenesulfonyl azides and cyanogen azide, mainly via ring contraction, with formation of the corresponding amidines. The mechanism of this efficient rearrangement, which has not been investigated experimentally, was determined with the aid of quantum-chemical calculations. In the transition state, from the intermediate 5-amino-v-triazolines, the loss of dinitrogen and a cyclic rearrangement occurred in one-step in a quite synchronous manner with a very low transition state energy.
    Mots-clés : 1, 2, 3-dipolar cycloadditions, 3-triazoles, Amidines, Azides, cascade, catalyst, chemistry, derivatives, Enamines, huisgen cycloaddition, ketones, organic azides, Quantum chemical calculations, Ring contraction, upsilon-triazolines.

  • Audran, G.; Bremond, P.; Marque, S. R. A.; Santelli, M. Tetrahedron 2017, 73 (25), 3492–3496.
    Résumé : Sulfur is one of the most necessary biogenic elements in nature that must be assimilated by all organisms; it is an essential macronutrient for living organisms and has multiple roles in plant development. The oxidation of elemental sulfur is a complex process involving the contact of cells with sulfur particles, the oxidation of sulfur to sulfite, and the oxidation of sulfite to sulfate. To provide hypothesis concerning the most probable processes in the early states, we determined, by quantum-chemical calculations, the energies of some allotropic forms containing up to 32-40 sulfur atoms and energetics of their reactions with triplet dioxygen. The most probable reactions occurred with methylpolysulfane anions with an electron transfer to give the superoxide anion radical (and thiyls radicals) and especially the formation of peroxydic polysulfane anions. Calculations confirmed that the triplet diradical is more stable than the singlet one for acyclic polysulfide chains. (C) 2017 Elsevier Ltd. All rights reserved.
    Mots-clés : base-catalyzed oxidation, batteries, Diradical sulfur chains, elemental sulfur, metabolism, oxidizing enzyme, Polysulfur derivatives, Quantum-chemical calculations, radical-anions, ray-absorption spectroscopy, rich oxides sno, Sulfur metabolism, sulfur oxygenase-reductase, Super oxide anion radical, thiobacillus-thiooxidans cells.
2016

  • Audran, G.; Bosco, L.; Bremond, P.; Butscher, T.; Franconi, J. - M.; Kabitaev, K.; Marque, S. R. A.; Mellet, P.; Parzy, E.; Santelli, M.; Thiaudiere, E.; Viel, S. Rsc Advances 2016, 6 (7), 5653-5670.
    Résumé : Recently, we published the titration of water in organic solvents and conversely using this family of nitroxides (Org. Biomol. Chem. 2015 ASAP). In this article, we show that the a(beta,P) of persistent cyclic beta-phosphorylated nitroxides decreases with the normalized polarity Reichardt's constant E-T(N). Koppel-Palm and Kalmet-Abboud-Taft relationships were applied to get a deeper insight into the effects influencing a(N) and a(beta,P): polarity/polarizability, hydrogen bond donor property, and structuredness of the cybotactic region.
    Mots-clés : aminoxyl radicals, bond homolysis, epr, esr, mri, nitrogen, polarity, probes, resonance, ring nitroxides.

  • Audran, G.; Bremond, P.; Marque, S. R. A.; Santelli, M. Tetrahedron Letters 2016, 57 (50), 5703-5706.
    Résumé : The dehydrodimerization of 2-butanone or 3-pentanone by lead dioxide leads to 3,4-dimethyl-2,5-hexanedione or 4,5-dimethyl-3,6-octanedione in nearly quantitative yield. This very clean and efficient reaction has been studied from mechanistic and stereochemical points of view. Dehydrodimerization of a 1:1 molar mixture of 2-butanone and 3-pentanone leads to 3,4-dimethyl-2,4-heptanedione in similar to 50% yield. From these gamma-diketones, 2,3,4-trimethylcyclopentenone, 3,4,5-trimethylcyclopentenone, 2,3,4,5-tetramethylcyclopentenone or 3-ethyl-2,4,5-trimethylcyclopentenone were obtained. (C) 2016 Elsevier Ltd. All rights reserved.
    Mots-clés : 1,2,3,4,5-pentamethylcyclopentadiene, 1,4-diketones, Acyl radical, carboxylic-acids, coupling reaction, Cyclization, Dehydrodimerization, gamma-Diketones, ketone, Lead dioxide, Photochemistry, stereochemistry, trimethylsilyl enol ethers.

  • Audran, G.; Bremond, P.; Marque, S. R. A.; Siri, D.; Santelli, M. Tetrahedron Letters 2016, 57 (16), 1743-1749.
    Résumé : As the well known protonated cyclopropanes' present calculations confirm the existence of acetylated cyclopropanes, we describe the structure of edge- and corner-acetylated cyclopropanes rising from the energetically favored addition of acetyl cation to cyclopropanes. Some of those explain the few available experimental results concerning the acetylation reaction of cyclopropanes. Structures have been calculated at the B3LYP/6-311++G(3df,3pd) and MP2/6-311++G(3df,3pd) levels of theory in ideal gas and in dichloromethane as solvent. Transition state geometries in ideal gas and in dichloromethane as solvent were confirmed by intrinsic reaction coordinate (IRC) calculations. (C) 2016 Elsevier Ltd. All rights reserved.
    Mots-clés : ab-initio, Acetylated cyclopropanes, acid, Acylation, biosynthesis, carbonium, cation, chemistry, Cyclopropanes, Intrinsic reaction coordinate (IRC) calculations, nonclassical carbocations, protonated cyclopropane, rearrangements, solvolytic reactions, Transition state.
2015

  • Audran, G.; Bosco, L.; Bremond, P.; Butscher, T.; Franconi, J. - M.; Marque, S. R. A.; Mellet, P.; Parzy, E.; Santelli, M.; Thiaudiere, E. Organic & Biomolecular Chemistry 2015, 13 (46), 11393-11400.
    Résumé : Recently, we showed that the phosphorus hyperfine coupling constant a(P beta) of persistent cyclic nitroxides decreased with the normalized polarity Reichardt's constant E-T(N). Thus, we investigated the changes in a(P beta) in binary mixtures of solvents. The sensitivity of a(P beta) to the solvent was high enough to allow us to perform water titration in THF, 1,4-dioxane, and acetonitrile by EPR. Accuracies of a few percent were achieved.

  • Audran, G.; Bremond, P.; El Abed, D.; Marque, S. R. A.; Siri, D.; Santelli, M. Helvetica Chimica Acta 2015, 98 (7), 1018-1027.
    Résumé : Energetics of intramolecular cycloadditions of azidoenynes and azidobutenenitriles to give 6H-pyrrolo[1,2-c][1,2,3]triazoles and 5H-pyrrolo[1,2-d]tetrazoles have been calculated at the B3LYP/6.311++G(3df,3pd) level of theory in ideal gas and in H2O as solvent. Stabilities of the corresponding anions, tautomers, and isomers are discussed. Transition states of the cyclization of parent compounds are determined at the same level of theory.

  • Audran, G.; Bremond, P.; Marque, S. R. A.; Siri, D.; Santelli, M. Tetrahedron 2015, 71 (38), 6920-6927.
    Résumé : Energetics of several various steps of the metabolisation of arachidonate anion into prostacyclins are been calculated at the B3LYP/6-311++G(3df,3pd) level of theory in ideal gas and in THF or water as solvents. Results clearly showed that prostaglandin G(2), resulting from enzymatic reactions of arachidonate anion with two molecules of dioxygen, is obtained after moderately exergonic processes (similar to 20 kcal mol(-1) overall) and therefore is a very reactive compound. After the action of the peroxidase active site of the cyclooxygenase, prostaglandin H-2 retains this high reactivity and the following isomerization steps giving rise to prostaglandin E-2, thromboxane A(2) and prostacyclin I-2, are highly exergonic reactions (>35 kcal mol(-1)). (C) 2015 Elsevier Ltd. All rights reserved.

  • Maurin, P.; Moraleda, D.; Pellissier, H.; Rodriguez, R.; Santelli, M. Synlett 2015, 26 (6), 725-736.
    Résumé : Lithium-mediated reductive dimerization of buta-1,3-diene in the presence of chloro(trimethyl)silane readily provides 1,8-bis(trimethylsilyl)octa-2,6-diene, commonly known as Bistro'. This bisallylsilane can react with various electrophilic reagents to give 1,1-disubstituted 2,5-divinylcyclopentanes, which are precursors of the D rings of steroids. After slight alterations, these precursors can be coupled with benzocyclobutene derivatives. Heat induces ring opening of the benzocyclobutene to form an o-xylylene that subsequently undergoes intramolecular cycloaddition with a vinyl substituent to form the skeleton of a new unnatural steroid, according to the A + D AD ABCD strategy. In this way, more than 250 steroids have been prepared, including 3-, 11-, 12-heterosteroids bearing a 17-vinyl group that can be readily modified to form a 17-acetyl or 17-(2-oxoethyl) group, as well as some steroid building blocks. The steroids were obtained in few steps from buta-1,3-diene and benzocyclobutene derivatives in overall yields in excess of 25%. This powerful strategy, which has not yet been exhausted, paves the way towards various related synthetic pathways. 1 Introduction 2 Series A 3 Series B 4 Series C 5 Series D 6 Series E 7 X-Ray Crystallographic Data 8 Conclusion
2014

  • Audran, G.; Bremond, P.; Marque, S. R. A.; Siri, D.; Santelli, M. Tetrahedron 2014, 70 (13), 2272-2279.
    Résumé : Concerning the Suzuki-Miyaura coupling reaction, we report detailed theoretical study of thermodynamic data (at the B3PW91/LANL2DZ level with polarization functions added and including dispersion force corrections) concerning each step of the catalytic cycle. In each case, we have observed a Hammett plotting of delta E or delta G versus sigma(p) of substituent of various reagents, which accounts for multiple-substituent effects. Therefore, these calculations predict the influence of the electron-donor/electron-acceptor character of each substituents on the thermodynamic requirements for reaction. Our major conclusion is that the transmetalation between a palladium hydroxo complex and an arylboronic acid is preferable to the transmetalation with a palladium bromo complex. Moreover, the alkaline hydrolysis of palladium bromo complex appears as a strong exothermic reaction. Concerning the reductive elimination step alternative processes have been investigated. The overall process giving rise to biphenyls appears as a very strong exothermic reaction (similar to-110 kcal/mol in ideal gas; similar to-95 kcal/mol using water as solvent). (c) 2014 Elsevier Ltd. All rights reserved.

  • Audran, G.; Bremond, P.; Marque, S. R. A.; Siri, D.; Santelli, M. Tetrahedron 2014, 70 (45), 8606-8613.
    Résumé : Polyunsaturated fatty acids like linolenic acid or arachidonic acid upon enzymatic hydroxylation (lipoxygenases) can lead to corresponding hydroperoxides. Their dehydration gave rise to vinyl allene oxides, which cyclized into cyclopentenones, precursors of jasmonic acid or prostanoids. We have studied the energetics of these cascade reactions to determine their thermodynamic parameters and reveal the key steps. The formation of hydroperoxydes from polyunsaturated fatty acids and triplet dioxygen appeared as a surprisingly slightly exergonic reaction (similar to 6-15 kcal mol(-1)). In contrast, the cumulated following reactions were highly exergonic (similar to 95-100 kcal mol(-1)). Cyclization of the (E)-vinyl allene oxides occurred with an activation barrier of similar to 23 kcal mol(-1), while cyclization of the (Z)-isomer required two steps: first isomerization into vinylcyclopropanone (TS: similar to 20 kcal mol(-1)), and then isomerization of the latter into cyclopentenone (TS: similar to 18 kcal mol(-1)). (C) 2014 Elsevier Ltd. All rights reserved.

  • Moraleda, D.; Galy, N.; Bremond, P.; Santelli, M. Comptes Rendus Chimie 2014, 17 (12), 1165-1168.
    Résumé : In the course of the Lewis acid-mediated cycloaddition of 1,8-bis(trimethylsilyl)-2,6-octadiene to bis-ketals, we have observed an unprecedented retro-Claisen condensation from the ketalisation of a 3-hydroxy-2,4-pentadione giving rise to a substituted 2,2,3-trimethoxybutane and an anti-Markovnikov stereoselective cycloaddition of the 1,8-bis(trimethylsily1)-2,6-octadiene to this latter ketal. (C) 2014 Academie des sciences. Published by Elsevier Masson SAS. All rights reserved.
2013

  • Aouf, C.; Galy, N.; Santelli, M. Tetrahedron 2013, 69 (15), 3225-3233.
    Résumé : The hydrolysis of beta-allenic tosylates produces mainly 2-methylenecyclobutanols resulting from a homoallenylic participation along with isomeric 2-methylenecyclobutanol minor products coming from a 1234-1243 rearrangement. Structures of various cyclopropylvinyl carbocations involved in the course of the hydrolysis have been determined by computational studies. For acyclic tosylates, the hydrolysis of one beta-deuterated allenic tosylate confirmed the nucleophilic attack on the corresponding nonclassical carbonium ion before its evolution to a more stable cyclopropylvinyl carbocation. In the case of one cyclic beta-allenic tosylate, the structure of the products has been checked by the use of deuterated isotopomer. (C) 2013 Published by Elsevier Ltd.

  • Audran, G.; Bremond, P.; Feuerstein, M.; Marque, S. R. A.; Santelli, M. Tetrahedron 2013, 69 (39), 8325-8348.

  • Audran, G.; Bremond, P.; Marque, S. R. A.; Gaudel-Siri, A.; Siri, D.; Santelli, M. Tetrahedron Letters 2013, 54 (48), 6607-6610.
    Résumé : Epoxidation of vinylallenes (1,2,4-pentatrienes) can lead to cyclopent-2-enones. Various experimental results suggest that these reactions are concerted and that vinylallene oxides undergo a concerted and thermal ring-closing reaction to give cyclopentenones. In 1977, this view has been supported by the epoxidation of a non-racemic 4-methyl-2,3,5-hexatriene to give a non-racemic 2,5-dimethy1-2-cyclopenten-1-one. Indeed, for the cyclization of (3E)-4-methyl-2,3-epoxy-2,3,5-hexatriene or (4-E)-4-methyl-3,4epoxy-2,3,5-hexatriene into 2,5-dimethy1-2-cyclopenten-1-one, a transition structure for the concerted rearrangement was located, and IRC calculations showed it linked together. The activation barrier predicted at the B3LYP/6-311++G(3df,3pd)//B3LYP/6-31G(d) level of theory is 80.9 or 124.2 kJ mol(-1), respectively and the reaction is exothermic by 127.2 or 89.2 kJ mol(-1), respectively. (C) 2013 Elsevier Ltd. All rights reserved.
2011

  • Aouf, C.; Santelli, M. Tetrahedron Letters 2011, 52 (6), 688-691.
    Résumé : The dibromocarbene or bromofluorocarbene addition to substituted allyldisilanes afforded instable gem-dibromocyclopropanes or a gem-bromofluorocyclopropane, respectively. These gem-bromohalogenocyclopropanes undergo a spontaneous ring opening at room temperature to give halogenated dienylsilanes or bromo dienes or dibromotetraenes. (C) 2010 Elsevier Ltd. All rights reserved.

  • Galy, N.; Doucet, H.; Santelli, M. Comptes Rendus Chimie 2011, 14 (5), 434-436.
    Résumé : Our recent experiments, for the formation of sodium amide from liquid ammonia and odium metal, revealed the necessity to employ Fe(NO(3))(3)center dot 9H(2)O as the catalyst precursor, and not FeCl(3). In the presence of FeCl(3), we observed several times the ignition of the mixture during the hydrolysis, and the desired product was not obtained. (C) 2010 Academie des sciences. Published by Elsevier Masson SAS. All rights reserved.

  • Galy, N.; Moraleda, D.; Santelli, M. Tetrahedron 2011, 67 (7), 1448-1455.
    Résumé : The bis-allylation of ethylene ketal and catechol ketal derivatives of 2,5-hexanedione occurred with a great stereoselectivity. The tetraallylation of bis-catechol ketal derivatives of 2,5-hexanedione and 2-methyl-1,3-cyclohexanedione or the diallylation of 4-phenylbutan-2-one derivatives arise in good yields and these compounds were suitable substrates for ring-closing metathesis leading to 4,4-dialkylcyclopentenes. Condensation of 1,8-bistrimethylsilyl-2,6-octadiene (Bistro) with 4-phenylbutan-2-one catechol ketal derivatives or 2-methylcyclohexan-1,3-dione mono catechol ketal afforded in good yields cyclic and tricyclic products 12 or 23, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  • Galy, N.; Santelli, M. Steroids 2011, 76 (7), 695-701.
    Résumé : We described an efficient synthesis of (8 beta,9 beta,14 beta)-17 beta-acetyl-13 beta-p-bromophenyl-11,11-di(methoxycarbonyl)-3-methoxygona-1,3,5(10)-tri ene, (8 beta,9 alpha,14 beta)-17 beta-acetyl-13 beta-p-bromophenyl-11,11-di(methoxycarbonyl)-3-methoxygona-1,3,5(10)-tri ene, (8 beta,9 beta,14 beta)-13 beta-p-bromophenyl-11,11-di(methoxycarbonyl)-17 beta-(2-hydroxyethyl)-3-methoxygona-1,3.5(10)-triene, and (8 beta,9 beta,14 beta)-13 beta-p-bromophenyl-11,11-di(methoxycarbonyl)-17 beta-(2-oxoxyethyl)-3-methoxygona-1,3,5(10)-triene in five or six steps from 1-iodo-4-methoxybenzocyclobutene and readily available materials. (C) 2011 Elsevier Inc. All rights reserved.

  • Reynaud, C.; Giorgi, M.; Doucet, H.; Santelli, M. Synthesis-Stuttgart 2011, Nᵒ 4, 674-680.
    Résumé : The Diels-Alder reaction of spirobicyclic cyclopentadiene derivatives, prepared by reaction of cyclopentadienyllithium and epichlorohydrin, with maleic anhydride gave a simple access to spiro tricyclic polyoxygenated compounds of synthetic interest. The solvolytic behavior of 1-(tosyloxymethyl)spiro[2.4]hepta-4,6-diene, a 5-spirocyclopentadiene, shows that the ionization of the tosylate was unlikely.
2010

  • Aouf, C.; Galy, N.; Doucet, H.; Santelli, M. Applied Organometallic Chemistry 2010, 24 (11), 794-797.
    Résumé : The reactivity for metathesis reaction of some polyunsaturated cyclopentanols, and of a polyunsaturated ketone bearing vinyl groups or vinyl and propenyl groups has been examined. In the presence of two of these reactants, depending on the ruthenium catalyst employed, either the ring closing metathesis or the cross-coupling metathesis was observed. Copyright (C) 2010 John Wiley & Sons, Ltd.

  • Chapelon, A. - S.; Giorgi, M.; Ollivier, C.; Santelli, M. Synthetic Communications 2010, 40 (1), 87-103.
    Résumé : trans-1,3-Divinylcyclopentanes bearing a -nitroalkyl chain (C2 or C3) in the 2-position were submitted to an intramolecular nitrile oxide cycloaddition process to give tricyclic isoxazoline precursors of 4-hydroxymethylbicyclo[3.3.0]octan-1-ol-3-ones or 5-hydroxymethyl-9-vinylbicyclo[4.3.0]nonan-1-ol-4-ones.

  • Fall, Y.; Doucet, H.; Santelli, M. Tetrahedron 2010, 66 (12), 2181-2188.
    Résumé : Five alkenylidenecyclopropanes have been arylated using a catalytic amount of [Pd(C3H5)Cl](2) (0.004%) associated to the tetradentate ligand cis, cis, cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane or Tedicyp as the catalyst The carbo-palladation step occurs on the terminal double bond of the vinyl-idenecyclopropanes, without interaction with the internal one The addition of the complex PdArL2 corresponds to an electrophilic attack on the face of the double bond. syn to the best election-donor cyclopropyl substituent (C) 2010 Elsevier Ltd All rights reserved

  • Fall, Y.; Doucet, H.; Santelli, M. Synthesis-Stuttgart 2010, Nᵒ 1, 127-135.
    Résumé : 1,3,5-Trisubstituted pyrazoles were found to be suitable partners for palladium-catalyzed direct arylation via C-H activation/functionalization using aryl bromides. The reaction conditions and the catalyst have a determining influence on the yields. The system using palladium(II) acetate as the catalyst, potassium acetate as the base, and N,N-dimethylacetamide as the solvent promotes selective 4-arylations in moderate to high yields. Several aryl and heteroaryl bromide derivatives have been employed successfully; their electronic properties have a decisive influence on the yields of coupling products. Electron-poor aryl bromides gave satisfactory results, whereas the electron-rich ones gave lower yields.

  • Galy, N.; Doucet, H.; Santelli, M. Tetrahedron Letters 2010, 51 (4), 695-697.
    Résumé : The C-2 molecule (1,2-ethynediyl) has been prepared by dehydrohalogenation of 1,2-dibromoethylene with an excess of potassium tert-butoxide in 2,3-dimethyl-2-butene as the solvent and the reagent. The major products of this reaction were 2,3-dimethylbut-3-en-2-ol and dibromoacetylene. (C) 2009 Elsevier Ltd. All rights reserved.

  • Moraleda, D.; Santelli, M. Journal of Physical Organic Chemistry 2010, 23 (8), 759-767.
    Résumé : The acylation of lithium (+/-)-spiro-gamma-lactone enolate 5 by the O-protected methyl (-)-(S)-lactate or the O-protected methyl (+)-(S)-mandelate occurs through enantio-differentiating reactions. The (S,S)-enolate 5 is the most reactive with the lactate whereas the (R,R)-enolate 5 selectively reacts with the mandelate. According to theoretical calculations at the B3LYP/6-31G(++)(d,p) level of theory of

  • Reynaud, C.; Doucet, H.; Santelli, M. Synthesis-Stuttgart 2010, Nᵒ 11, 1787-1792.
    Résumé : The Diels-Alder reaction of some bromo derivatives of the itaconic acid with cyclopenta-1,3-diene gave a simple access to precursors of spherical polyols of synthetic interest.

  • Reynaud, C.; Giorgi, M.; Doucet, H.; Santelli, M. Tetrahedron 2010, 66 (23), 4101-4108.
    Résumé : The ozonation of four bornene derivatives, prepared from (R)-(+)-pulegone, which possess a particularly hindered double bond, led to the formation of unexpected products depending on the nature of the solvent. The formation of the corresponding epoxides, ketones with the same skeleton, various lactones and even an allyl alcohol and an allyl chloride (allylic functionalisation) was observed. In two cases, products presenting a pulegone modified skeleton resulting from a Wagner-Meerwein rearrangement were obtained. The structure of three products was confirmed by crystallographic X-ray analysis. Mechanisms taking into account the rigid and congested structure of the reactants explain these results. The most striking steps were backed up by theoretical calculations. (C) 2010 Elsevier Ltd. All rights reserved.
  • Santelli, M. Actualite Chimique 2010, Nᵒ 346, 36-37.
    Résumé : The ozone layer discovery: a Marseilles story... The ozone layer discovery occurred at the Faculty of sciences of Marseilles in 1913 by Charles Fabry and Henri Buisson. Moreover, Fabry predicted that this ozone layer was present in the troposphere. A short comment concerning the ozone generation as a greenhouse gas is given.