Pub Date : 2001-08-01DOI: 10.1016/S1387-1609(01)01288-9
Joumana Toufaily, Michel Soulard, Jean-Louis Guth
Heteropolyacids (HPW) are known as active catalysts for various redox reactions. The direct incorporation of HPW species in a mesoporous organised silica molecular sieve during the synthesis was studied. The association of two type of surfactants is essential for the preparation of such solids. The silica-organised materials comprising heteropoly compounds thus obtained were thermally stable porous materials with mesopores and large surface areas.
{"title":"Étude physicochimique de nouveaux composés formés par incorporation directe d’hétéropolyacide dans une silice mésoporeuse organisée","authors":"Joumana Toufaily, Michel Soulard, Jean-Louis Guth","doi":"10.1016/S1387-1609(01)01288-9","DOIUrl":"10.1016/S1387-1609(01)01288-9","url":null,"abstract":"<div><p>Heteropolyacids (HPW) are known as active catalysts for various redox reactions. The direct incorporation of HPW species in a mesoporous organised silica molecular sieve during the synthesis was studied. The association of two type of surfactants is essential for the preparation of such solids. The silica-organised materials comprising heteropoly compounds thus obtained were thermally stable porous materials with mesopores and large surface areas.</p></div>","PeriodicalId":100305,"journal":{"name":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","volume":"4 8","pages":"Pages 675-681"},"PeriodicalIF":0.0,"publicationDate":"2001-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/S1387-1609(01)01288-9","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"88894774","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
In our program of new macrocyclic antibiotic derivatives synthesis, a natural kijamicin analog was isolated, disclosing important antibiotic and antiviral properties, which are under investigation. In this paper we describe a synthesis of the bottom half C1-C14 (n = 1) of its aglycon. This strategy was based on the preparation of a tetraene derivative via a palladium catalyzed Stille coupling reaction, the final step involving an IMDA cyclization key step.
{"title":"IMDA reaction in a synthetic approach towards a natural kijamicin aglycon analog","authors":"Jean-François Betzer, Janick Ardisson, Ange Pancrazi","doi":"10.1016/S1387-1609(01)01260-9","DOIUrl":"10.1016/S1387-1609(01)01260-9","url":null,"abstract":"<div><p>In our program of new macrocyclic antibiotic derivatives synthesis, a natural kijamicin analog was isolated, disclosing important antibiotic and antiviral properties, which are under investigation. In this paper we describe a synthesis of the bottom half C1-C14 (<em>n</em> = 1) of its aglycon. This strategy was based on the preparation of a tetraene derivative via a palladium catalyzed Stille coupling reaction, the final step involving an IMDA cyclization key step.</p></div>","PeriodicalId":100305,"journal":{"name":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","volume":"4 8","pages":"Pages 695-704"},"PeriodicalIF":0.0,"publicationDate":"2001-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/S1387-1609(01)01260-9","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"83486845","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2001-08-01DOI: 10.1016/S1387-1609(01)01280-4
Jameleddine Khiari , Béchir Ben Hassine , Denis Gravel
An efficient synthesis of two analogues of huperzine A via a one-step synthesis of E alkene.
一步法合成石杉碱A的两个类似物。
{"title":"Méthodologie de synthèse des analogues à chaînes ouvertes de l’huperzine A","authors":"Jameleddine Khiari , Béchir Ben Hassine , Denis Gravel","doi":"10.1016/S1387-1609(01)01280-4","DOIUrl":"10.1016/S1387-1609(01)01280-4","url":null,"abstract":"<div><p>An efficient synthesis of two analogues of huperzine A via a one-step synthesis of <em>E</em> alkene.</p></div>","PeriodicalId":100305,"journal":{"name":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","volume":"4 8","pages":"Pages 705-710"},"PeriodicalIF":0.0,"publicationDate":"2001-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/S1387-1609(01)01280-4","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"85494780","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2001-08-01DOI: 10.1016/S1387-1609(01)01284-1
Henri Rudler, Andrée Parlier, Victor Certal, Jean-Cédric Frison
The dihydropyridine-induced reduction of alkoxycarbene complexes of chromium has been generalized to differently substituted dihydropyridines, e.g. N-benzyl dihydropyridine and N-methyl-N’N’-diethyldihydronicotinamide. In all the cases examined, alkoxyalkynyl carbene complexes lead, upon cascade insertions, to butenolides, the diastereomeric excesses being dependent on the structure of the dihydropyridines.
二氢吡啶诱导的铬烷氧羰基配合物的还原已推广到不同取代的二氢吡啶,如n -苄基二氢吡啶和n -甲基- n ' n ' -二乙基二氢烟碱酰胺。在所研究的所有案例中,烷氧炔基羰基羰基配合物通过级联插入导致丁烯内酯,非对映异构体的过量依赖于二氢吡啶的结构。
{"title":"Functionalized dihydropyridines do reduce alkoxycarbene complexes of chromium and give access to polycyclic butenolides","authors":"Henri Rudler, Andrée Parlier, Victor Certal, Jean-Cédric Frison","doi":"10.1016/S1387-1609(01)01284-1","DOIUrl":"10.1016/S1387-1609(01)01284-1","url":null,"abstract":"<div><p>The dihydropyridine-induced reduction of alkoxycarbene complexes of chromium has been generalized to differently substituted dihydropyridines, e.g. <em>N</em>-benzyl dihydropyridine and <em>N</em>-methyl-<em>N’N’</em>-diethyldihydronicotinamide. In all the cases examined, alkoxyalkynyl carbene complexes lead, upon cascade insertions, to butenolides, the diastereomeric excesses being dependent on the structure of the dihydropyridines.</p></div>","PeriodicalId":100305,"journal":{"name":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","volume":"4 8","pages":"Pages 671-674"},"PeriodicalIF":0.0,"publicationDate":"2001-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/S1387-1609(01)01284-1","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"72692728","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2001-08-01DOI: 10.1016/S1387-1609(01)01266-X
Benoît E Prieur
Boric acid has always been neglected in prebiotic chemistry, because it is not a major component of biological macromolecules. We argue here for a potential catalytic role of boric acid in peptides and nucleic acid synthesis. Today boron is an important component of seawater (0.4 mM). Its concentration at prebiotic times was probably higher. In water, boron mainly appears in the form of boric acid or its derivatives (esters and anhydrides).
{"title":"Étude de l’activité prébiotique potentielle de l’acide borique","authors":"Benoît E Prieur","doi":"10.1016/S1387-1609(01)01266-X","DOIUrl":"10.1016/S1387-1609(01)01266-X","url":null,"abstract":"<div><p>Boric acid has always been neglected in prebiotic chemistry, because it is not a major component of biological macromolecules. We argue here for a potential catalytic role of boric acid in peptides and nucleic acid synthesis. Today boron is an important component of seawater (0.4 mM). Its concentration at prebiotic times was probably higher. In water, boron mainly appears in the form of boric acid or its derivatives (esters and anhydrides).</p></div>","PeriodicalId":100305,"journal":{"name":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","volume":"4 8","pages":"Pages 667-670"},"PeriodicalIF":0.0,"publicationDate":"2001-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/S1387-1609(01)01266-X","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"89461003","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2001-08-01DOI: 10.1016/S1387-1609(01)01291-9
Yves Jeannin
By mixing an aqueous solution of antimonotungstate at pH = 4–5 and an aqueous solution of manganese(II) chloride, of cobalt(II) chloride, of nickel(II) chloride, or of zinc, a monosubstituted heteropolytungstate 〚H3SbIIIMIIW17O59(H2O)〛8– is obtained (MII = MnII, CoII, NiII, ZnII). The crystallographic study, associated to EPR, XANES, EXAFS, and proton NMR spectrometries, leads to a structure identical to this of 〚H2AsIIIW18O60〛7–. There are two moieties SbIIIW9O30 and H3MIIW8O30. It is concluded that the MII atom substitutes a tungsten atom of the belt of six octahedra perpendicular to the ternary axis of the polytungstate. The same type of compound was obtained starting from bismuth chloride and copper acetate, that is 〚H3BiIIICuIIW17O59(H2O)〛8–.
{"title":"Synthèse et étude structurale d’un nouvel hétéropolytungstate substitué Na8〚H3XIIIMIIW17O59(H2O)〛·36 H2O (X = SbIII, BiIII et M = Mn2+, Co2+, Ni2+, Cu2+, Zn2+) de structure identique à celle de 〚H2XIIIW18O60〛7– (X = As, Bi)","authors":"Yves Jeannin","doi":"10.1016/S1387-1609(01)01291-9","DOIUrl":"10.1016/S1387-1609(01)01291-9","url":null,"abstract":"<div><p>By mixing an aqueous solution of antimonotungstate at pH = 4–5 and an aqueous solution of manganese(II) chloride, of cobalt(II) chloride, of nickel(II) chloride, or of zinc, a monosubstituted heteropolytungstate 〚H<sub>3</sub>Sb<sup>III</sup>M<sup>II</sup>W<sub>17</sub>O<sub>59</sub>(H<sub>2</sub>O)〛<sup>8–</sup> is obtained (M<sup>II</sup> = Mn<sup>II</sup>, Co<sup>II</sup>, Ni<sup>II</sup>, Zn<sup>II</sup>). The crystallographic study, associated to EPR, XANES, EXAFS, and proton NMR spectrometries, leads to a structure identical to this of 〚H<sub>2</sub>As<sup>III</sup>W<sub>18</sub>O<sub>60</sub>〛<sup>7–</sup>. There are two moieties Sb<sup>III</sup>W<sub>9</sub>O<sub>30</sub> and H<sub>3</sub>M<sup>II</sup>W<sub>8</sub>O<sub>30</sub>. It is concluded that the M<sup>II</sup> atom substitutes a tungsten atom of the belt of six octahedra perpendicular to the ternary axis of the polytungstate. The same type of compound was obtained starting from bismuth chloride and copper acetate, that is 〚H<sub>3</sub>Bi<sup>III</sup>Cu<sup>II</sup>W<sub>17</sub>O<sub>59</sub>(H<sub>2</sub>O)〛<sup>8–</sup>.</p></div>","PeriodicalId":100305,"journal":{"name":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","volume":"4 8","pages":"Pages 683-690"},"PeriodicalIF":0.0,"publicationDate":"2001-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/S1387-1609(01)01291-9","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"73478831","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2001-08-01DOI: 10.1016/S1387-1609(01)01265-8
François Bouyssi , Jean Jacques
From Jean-Baptiste Dumas to Chaïm Weizmann and to Margaret Thatcher, including Alfred Naquet, Marcelin Berthelot, Auguste Scheurer-Kaster, Stanislao Cannizzaro, Frédéric Joliot etc., there are few chemists who, at one time or another, have not been tempted to enter politics. Philippe Landrieu is certainly one of the lesser known of this group, even if he had a laudatory Obituary in both the Bulletin de la Société chimique de France, and La Nouvelle Revue socialiste. The events in which he was involved, the utopias for which he was searching, his double career, and his scientific work, nothing was ordinary in his busy life. This Note, as well as placing him in the social history of the last century, will also recall his work as a chemist, and the unresolved problems in which he was interested.
{"title":"Philippe Landrieu (1872–1926), un chimiste engagé dans la politique expérimentale","authors":"François Bouyssi , Jean Jacques","doi":"10.1016/S1387-1609(01)01265-8","DOIUrl":"10.1016/S1387-1609(01)01265-8","url":null,"abstract":"<div><p>From Jean-Baptiste Dumas to Chaïm Weizmann and to Margaret Thatcher, including Alfred Naquet, Marcelin Berthelot, Auguste Scheurer-Kaster, Stanislao Cannizzaro, Frédéric Joliot etc., there are few chemists who, at one time or another, have not been tempted to enter politics. Philippe Landrieu is certainly one of the lesser known of this group, even if he had a laudatory Obituary in both the <em>Bulletin de la Société chimique de France</em>, and <em>La Nouvelle Revue socialiste</em>. The events in which he was involved, the utopias for which he was searching, his double career, and his scientific work, nothing was ordinary in his busy life. This Note, as well as placing him in the social history of the last century, will also recall his work as a chemist, and the unresolved problems in which he was interested.</p></div>","PeriodicalId":100305,"journal":{"name":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","volume":"4 8","pages":"Pages 717-721"},"PeriodicalIF":0.0,"publicationDate":"2001-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/S1387-1609(01)01265-8","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"79704156","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2001-08-01DOI: 10.1016/S1387-1609(01)01290-7
Adyl Oussaid, Patricia Garrigues, Bernard Garrigues
Bismuth(III) salts as catalysts in the ether cleavage reaction. Bi (OTf)3 and BiCl3 react in catalytic quantity to cleaved the tertiobutyl–oxygen bound of the ethers 1, 3, 5.
{"title":"Les sels de bismuth(III), catalyseurs dans la réaction de clivage des éthers","authors":"Adyl Oussaid, Patricia Garrigues, Bernard Garrigues","doi":"10.1016/S1387-1609(01)01290-7","DOIUrl":"10.1016/S1387-1609(01)01290-7","url":null,"abstract":"<div><p>Bismuth(III) salts as catalysts in the ether cleavage reaction. Bi (OTf)<sub>3</sub> and BiCl<sub>3</sub> react in catalytic quantity to cleaved the tertiobutyl–oxygen bound of the ethers 1, 3, 5.</p></div>","PeriodicalId":100305,"journal":{"name":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","volume":"4 8","pages":"Pages 691-694"},"PeriodicalIF":0.0,"publicationDate":"2001-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/S1387-1609(01)01290-7","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"79025236","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2001-08-01DOI: 10.1016/S1387-1609(01)01285-3
Henri-Jean Cristau, Michel Carteron, Alain Fruchier, Jean-Luc Pirat
The stereochemistry of the ring opening of (R,S) or (R,R)-4,5-dimethyl-2,2,2-triphenyl-1,3,2λ5-dioxaphospholanes (prepared by reaction of (R,S) or (R,R)-butane-2,3-diol with dibromotriphenylphosphorane) by aniline or thiophenol was investigated. The reaction affords stereoselectively the corresponding β-anilino- or β-phenylthioalcohols with a nearly complete inversion of stereochemistry at the stereogenic reaction centre.
{"title":"Diastereospecific synthesis of β-heterosubstituted alcohols from 1,2-diols via 1,3,2λ5-dioxaphospholanes","authors":"Henri-Jean Cristau, Michel Carteron, Alain Fruchier, Jean-Luc Pirat","doi":"10.1016/S1387-1609(01)01285-3","DOIUrl":"10.1016/S1387-1609(01)01285-3","url":null,"abstract":"<div><p>The stereochemistry of the ring opening of <em>(R,S)</em> or <em>(R,R)</em>-4,5-dimethyl-2,2,2-triphenyl-1,3,2λ<sup>5</sup>-dioxaphospholanes (prepared by reaction of <em>(R,S)</em> or <em>(R,R)</em>-butane-2,3-diol with dibromotriphenylphosphorane) by aniline or thiophenol was investigated. The reaction affords stereoselectively the corresponding β-anilino- or β-phenylthioalcohols with a nearly complete inversion of stereochemistry at the stereogenic reaction centre.</p></div>","PeriodicalId":100305,"journal":{"name":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","volume":"4 8","pages":"Pages 711-715"},"PeriodicalIF":0.0,"publicationDate":"2001-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/S1387-1609(01)01285-3","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"82891706","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2001-07-01DOI: 10.1016/S1387-1609(01)01269-5
Hideo Togo , Masaaki Sugi , Ken-ichi Toyama
The synthetic utility of 1,1,2,2-tetraphenyldisilane as a new, environmentally benign radical mediator is discussed for the reduction, cyclization, reductive addition to olefins, and alkylation of heteroaromatic bases.
{"title":"1,1,2,2-Tetraphenyldisilane (TPDS) as a new diversified radical reagent","authors":"Hideo Togo , Masaaki Sugi , Ken-ichi Toyama","doi":"10.1016/S1387-1609(01)01269-5","DOIUrl":"10.1016/S1387-1609(01)01269-5","url":null,"abstract":"<div><p>The synthetic utility of 1,1,2,2-tetraphenyldisilane as a new, environmentally benign radical mediator is discussed for the reduction, cyclization, reductive addition to olefins, and alkylation of heteroaromatic bases.</p></div>","PeriodicalId":100305,"journal":{"name":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","volume":"4 7","pages":"Pages 539-546"},"PeriodicalIF":0.0,"publicationDate":"2001-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/S1387-1609(01)01269-5","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"73433606","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}