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Synthesis of Endothiopeptides by Using the 'Azirine/Oxazolone Method' “叠嗪/恶唑酮法”合成内硫肽
Polish Journal of Chemistry Pub Date : 2009-01-01 DOI: 10.5167/UZH-12664
A. Bärtsch, B. Bischof, H. Heimgartner
{"title":"Synthesis of Endothiopeptides by Using the 'Azirine/Oxazolone Method'","authors":"A. Bärtsch, B. Bischof, H. Heimgartner","doi":"10.5167/UZH-12664","DOIUrl":"https://doi.org/10.5167/UZH-12664","url":null,"abstract":"The reaction of tert-butyl- or THP-protected mandelic thioacid (7a and 7b) with N,N,2,2-tetramethyl-2H-azirin-3-amine (2a) gave the dipeptide analogues tBu- and THP-Mns-Aibψ[CS]NMe 2 (8a and 8b, resp.) with a C-terminal thioamide group. Treatment of 8a with HCl gas in toluene led to 2-(1-rert-butoxybenzyl)-4,4-dimethyl-1,3-thiazole-5(4H)-one (9), which reacted with dimethylamine via ring opening to give tBu-Mnsψ[CSNH]Aib-NMe2 (lla), an isomer of8a with the thioamide group within the chain, i.e., the product of a sulfur migration. In the case of 8b, selective deprotection of the THP-hydroxy group was achieved by treatment with pyridinium p-toluenesulfonate (PPTS) in ethanol. Cyclization of the resulting Mns-Aibψ[CS]NMe 2 (13) yielded the 2-thioxomorpholin-5-one 10. In a similar manner, Boc-Val-SH (14) reacted with azirine 2b to give Boc-Val-Aibψ[CS]N(Me)Ph (15a), which was transformed to Fmoc-Val-Aibψ[CS]N(Me)Ph (15b) and further to Fmoc-Valψ[CSNH]Aib-N(Me)Ph (16) by treatment with ZnCl 2 in acetic acid. Coupling of two of these molecules via the 1,3-thiazol-5(4H)-one 17 yielded the endodithiopeptide Fmoc-Valψ[CSNH]Aib-Valψ[CSNH]Aib-N(Me)Ph (19).","PeriodicalId":20369,"journal":{"name":"Polish Journal of Chemistry","volume":"83 1","pages":"195-206"},"PeriodicalIF":0.0,"publicationDate":"2009-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"70638389","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}
引用次数: 4
Ambivalent Nucleophilicity of 1,4,5-Trisubstituted Imidazole-2-thiones in Reactions with Dimethyl Acetylenedicarboxylate and Phenylisocyanate 1,4,5-三取代咪唑-2-硫酮与二甲基乙酰二羧酸酯和苯基异氰酸酯反应的亲核性
Polish Journal of Chemistry Pub Date : 2008-01-01 DOI: 10.5167/UZH-12637
G. Mlostoń, T. Gendek, A. Linden, H. Heimgartner
{"title":"Ambivalent Nucleophilicity of 1,4,5-Trisubstituted Imidazole-2-thiones in Reactions with Dimethyl Acetylenedicarboxylate and Phenylisocyanate","authors":"G. Mlostoń, T. Gendek, A. Linden, H. Heimgartner","doi":"10.5167/UZH-12637","DOIUrl":"https://doi.org/10.5167/UZH-12637","url":null,"abstract":"The 1,4,5-trisubstitued 2,3-dihydro-1H-imidazole-2-thiones 1 react with electrophilic reagents via the S- or the N(3)-atom. The reaction with dimethyl acetylenedicarboxylate in methanol at room temperature occurs by the nucleophilic addition of the S-atom to give the corresponding 2-[(1H-imidazol-2-yl)sulfanyl]fumarates 4 in high yield. On the other hand, imidazole-2-thiones 1 react with phenylisocyanate in dichloromethane at room temperature to yield 2,3-dihydro-2-thioxo-1H-imidazole-1-carboxamides 5. The structures of both types of adducts were established by X-ray crystallography.","PeriodicalId":20369,"journal":{"name":"Polish Journal of Chemistry","volume":"82 1","pages":"1561-1569"},"PeriodicalIF":0.0,"publicationDate":"2008-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"70638058","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}
引用次数: 3
Synthesis of 1,3-Oxaselenan-2-imines from Isoselenocyanates 由异硒氰酸酯合成1,3-草甘膦-2-亚胺
Polish Journal of Chemistry Pub Date : 2007-01-01 DOI: 10.5167/UZH-50676
G. Sommen, H. Heimgartner
{"title":"Synthesis of 1,3-Oxaselenan-2-imines from Isoselenocyanates","authors":"G. Sommen, H. Heimgartner","doi":"10.5167/UZH-50676","DOIUrl":"https://doi.org/10.5167/UZH-50676","url":null,"abstract":"The reactions ofaryl isoselenocyanates 1 with 3-chloropropan- 1-ol (8) in the presence of sodium hydride in dichloromethane at room temperature gave 1,3-oxaselenan-2-imines 10 in fair yield. A reaction mechanism via nucleophilic attack of the alcoholate at the isoselenocyanate 1, followed by an 6-exo-teτ cyclization, is most likely.","PeriodicalId":20369,"journal":{"name":"Polish Journal of Chemistry","volume":"81 1","pages":"1413-1418"},"PeriodicalIF":0.0,"publicationDate":"2007-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"70654484","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}
引用次数: 7
Crystal Structure of Terbium Potassium Octacyanotungstate(IV) Heptahydrate 七水合八氰钨酸铽钾的晶体结构
Polish Journal of Chemistry Pub Date : 2007-01-01 DOI: 10.1002/CHIN.200816005
H. Stoeckli-Evans, I. Typilo, D. Semenyshyn, O. Sereda, R. Gladyshevskii
{"title":"Crystal Structure of Terbium Potassium Octacyanotungstate(IV) Heptahydrate","authors":"H. Stoeckli-Evans, I. Typilo, D. Semenyshyn, O. Sereda, R. Gladyshevskii","doi":"10.1002/CHIN.200816005","DOIUrl":"https://doi.org/10.1002/CHIN.200816005","url":null,"abstract":"Thallium sulfide layers will be formed on the surface of low-density polyethylene (PE) if the PE layer is sulphured in a solution of higher polythionic acid H 2 S 33 O 6 , and then immersed in the alkaline solution of thallium(Ι) sulfate. Sulphur concentration increases on PE surface with the increase of the sulphurization time. The amount of thallium in the Tl x S y layers depends on a sulphur concentration sorbed-diffused into PE. Three phases TlS, Tl 2 S and Tl 2 S 2 were identified by X-ray diffraction analysis in thallium sulfide layers. Scanning Electron (SEM) and Atomic Force (AFM) microscopies were used to characterize surface morphology of thallium sulfide layers. The films deposited on the PE surface have a non-homogeneous structure and consist of separated islands. The process of their growth on PE surface starts from nucleation sites creating islands of TlS with diameter in tenths of microns which increase up to 9 μm during 1 h deposition.","PeriodicalId":20369,"journal":{"name":"Polish Journal of Chemistry","volume":"81 1","pages":"2031-2038"},"PeriodicalIF":0.0,"publicationDate":"2007-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/CHIN.200816005","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"51055023","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}
引用次数: 6
Electrooxidative Conversion of Dibenzoylbenzene Dihydrazones into the Coreesponding Bis-Diazo Compounds and Bis-Dimethyl Acetals 二苯甲酰苯二腙电氧化转化为核心响应的双重氮化合物和双二甲基缩醛
Polish Journal of Chemistry Pub Date : 2005-08-01 DOI: 10.1071/CH05090
M. Okimoto, K. Numata, Y. Takahashi
{"title":"Electrooxidative Conversion of Dibenzoylbenzene Dihydrazones into the Coreesponding Bis-Diazo Compounds and Bis-Dimethyl Acetals","authors":"M. Okimoto, K. Numata, Y. Takahashi","doi":"10.1071/CH05090","DOIUrl":"https://doi.org/10.1071/CH05090","url":null,"abstract":"Several dibenzoylbenzene dihydrazones were electrochemically oxidized into the corresponding bis-dimethyl acetals in a methanolic solution containing sodium methoxide and catalytic amount of KI. During electrolysis, the anolyte exhibited a characteristic deep purple, which strongly suggested that formation of a diazo compound as an intermediate. Interestingly, some of the diazo compounds could be isolated directly from the anolyte.","PeriodicalId":20369,"journal":{"name":"Polish Journal of Chemistry","volume":"79 1","pages":"1477-1482"},"PeriodicalIF":0.0,"publicationDate":"2005-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1071/CH05090","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"58662895","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}
引用次数: 7
Addition of Diazomethane to Phosphonodithioformates and Reactions of Phosphonylated Thiocarbonyl S-Methylides 重氮甲烷在二硫代甲酸膦酸盐中的加成及膦化硫羰基s -甲基的反应
Polish Journal of Chemistry Pub Date : 2005-01-01 DOI: 10.5167/UZH-67591
K. Urbaniak, G. Mlostoń, M. Gulea, S. Masson*, H. Heimgartner
{"title":"Addition of Diazomethane to Phosphonodithioformates and Reactions of Phosphonylated Thiocarbonyl S-Methylides","authors":"K. Urbaniak, G. Mlostoń, M. Gulea, S. Masson*, H. Heimgartner","doi":"10.5167/UZH-67591","DOIUrl":"https://doi.org/10.5167/UZH-67591","url":null,"abstract":"The reaction of phosphonodithioformates 14 with diazomethane at –60°C yielded 2,5-dihydro-1,3,4-thiadiazoles 15 as unstable intermediates. Their structure was evidenced by the base-catalyzed elimination of methylsulfane leading to 1,3,4-thiadiazole-2-phosphonates. At ca. –35°C, thermal decomposition of 15 by N2-elimination led to reactive thiocarbonyl S-methylides 17. In the absence of trapping reagents, these 1,3-dipoles undergo a head-to-head dimerization leading to 1,4-dithianes 18. An intermediate zwitterionic dimer 19 was detected by 31P NMR spectroscopy. The initially formed thiocarbonyl S-methylide 17 as well as an open-chain zwitterionic dimer 20 was intercepted by methanol. Stable interception products were also obtained with S- and N-nucleophiles.","PeriodicalId":20369,"journal":{"name":"Polish Journal of Chemistry","volume":"79 1","pages":"1483-1494"},"PeriodicalIF":0.0,"publicationDate":"2005-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"70659845","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}
引用次数: 6
Methanol Synthesis from CO2 and H2 on Cu/ZnO/Al2O3-ZrO2 Catalysts. Catalytic Activity and Adsorption of Reactants Cu/ZnO/Al2O3-ZrO2催化剂上CO2和H2合成甲醇催化活性和吸附反应物
Polish Journal of Chemistry Pub Date : 2001-01-01 DOI: 10.1016/s0140-6701(02)80247-8
J. Słoczyński
{"title":"Methanol Synthesis from CO2 and H2 on Cu/ZnO/Al2O3-ZrO2 Catalysts. Catalytic Activity and Adsorption of Reactants","authors":"J. Słoczyński","doi":"10.1016/s0140-6701(02)80247-8","DOIUrl":"https://doi.org/10.1016/s0140-6701(02)80247-8","url":null,"abstract":"","PeriodicalId":20369,"journal":{"name":"Polish Journal of Chemistry","volume":"75 1","pages":"733-742"},"PeriodicalIF":0.0,"publicationDate":"2001-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/s0140-6701(02)80247-8","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"55841683","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}
引用次数: 8
Physical and Chemical Properties RElated to Defect Structure of Oxides and Silicates Doped with Water and Carbon Dioxide 掺杂水和二氧化碳的氧化物和硅酸盐缺陷结构的理化性质
Polish Journal of Chemistry Pub Date : 2001-01-01 DOI: 10.1016/S0074-6142(01)80095-4
S. Malinowski
{"title":"Physical and Chemical Properties RElated to Defect Structure of Oxides and Silicates Doped with Water and Carbon Dioxide","authors":"S. Malinowski","doi":"10.1016/S0074-6142(01)80095-4","DOIUrl":"https://doi.org/10.1016/S0074-6142(01)80095-4","url":null,"abstract":"","PeriodicalId":20369,"journal":{"name":"Polish Journal of Chemistry","volume":"77 1","pages":"609-626"},"PeriodicalIF":0.0,"publicationDate":"2001-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/S0074-6142(01)80095-4","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"55809495","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}
引用次数: 3
THE REACTION OF SOME DITHIINODIQUINOLINES WITH POTASSIUM METHOXIDE AS A SOURCE OF 4-QUINOLINONES WITH 3-SULFIDE FUNCTION 一些二硫代二喹啉与甲氧基钾反应生成具有3-硫化物功能的4-喹啉酮
Polish Journal of Chemistry Pub Date : 2000-02-22 DOI: 10.1002/CHIN.200008162
A. Maślakiewicz, E. Bębenek
{"title":"THE REACTION OF SOME DITHIINODIQUINOLINES WITH POTASSIUM METHOXIDE AS A SOURCE OF 4-QUINOLINONES WITH 3-SULFIDE FUNCTION","authors":"A. Maślakiewicz, E. Bębenek","doi":"10.1002/CHIN.200008162","DOIUrl":"https://doi.org/10.1002/CHIN.200008162","url":null,"abstract":"","PeriodicalId":20369,"journal":{"name":"Polish Journal of Chemistry","volume":"1 1","pages":"1783-1789"},"PeriodicalIF":0.0,"publicationDate":"2000-02-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/CHIN.200008162","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"50951051","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}
引用次数: 2
Stereochemistry of new nitrogen containg heterocyclicaldehydes. III. Novel bis-bidentate azodye compounds 新型含氮杂环醛的立体化学。3新型双双齿偶氮染料化合物
Polish Journal of Chemistry Pub Date : 1999-07-01 DOI: 10.1080/00387019909350008
A. F. Shoair, A. El‐Bindary, A. El-Sonbati, R. Younes
{"title":"Stereochemistry of new nitrogen containg heterocyclicaldehydes. III. Novel bis-bidentate azodye compounds","authors":"A. F. Shoair, A. El‐Bindary, A. El-Sonbati, R. Younes","doi":"10.1080/00387019909350008","DOIUrl":"https://doi.org/10.1080/00387019909350008","url":null,"abstract":"Abstract A novel family of chelating bis-bidentate azodye compounds1 with Cu(II), Co(II), Ni(II), Fe(II), Hg(II), Pd(II), UO2(II), Fe(III), Cr(III), La(III), Ru(III) and Zr(IV) has been prepared and characterized on the basis of analytical, magnetic, 1H and 13C NMR, EPR and electronic spectral studies. Tentative structures for the polymeric complexes are proposed. The important IR bands and the main 1H and 13C signals are assigned and discussed relative to the molecular structure. Various EPR parameters for Cμ(II), have been calculated. The ligand acts as a dibasic bis-bidentate chelating agent coordinating through CO, N=N, COOH and OH groups by replacement of a proton from the two latter groups. Considerable interest has also been focused on the synthesis of the azo compound and its polymeric metal complex due to its wide potential applications. The thermal decomposition behavior of the complexes is also discussed.","PeriodicalId":20369,"journal":{"name":"Polish Journal of Chemistry","volume":"74 1","pages":"1047-1053"},"PeriodicalIF":0.0,"publicationDate":"1999-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/00387019909350008","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"59182972","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}
引用次数: 22
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