Pub Date : 2017-02-17DOI: 10.1080/10426507.2017.1292273
J. Voss, D. Otzen, G. Adiwidjaja
GRAPHICAL ABSTRACT ABSTRACT Methyl 3,5-anhydro-3-thiopentofuranosides (“3,5-Thietanopentosides”) of the D-xylo, L-lyxo and 2-deoxy-D-threo series were oxidized to the corresponding S-oxides (sulfoxides) and/or S,S-dioxides (sulfones) by use of hydrogen peroxide or meta-chloroperbenzoic acid. The diastereoisomers resulting from the additional chiral sulfur center in the sulfoxides could be separated. Their configuration was assigned by NMR spectroscopy and in one case unequivocally corroborated by an X-ray structure analysis. The observed stereoselectivity of the oxidation can be attributed to the specific steric requirements in the different thietano sugars. X-Ray structural analyses of three crystalline sulfones were also performed. Attempts to generate carbanions of the sulfoxides and sulfones and to use these for reactions with electrophiles were not successful.
{"title":"3,5-Thietanopentofuranoside S-oxides and S,S-dioxides – preparation and structural characterization","authors":"J. Voss, D. Otzen, G. Adiwidjaja","doi":"10.1080/10426507.2017.1292273","DOIUrl":"https://doi.org/10.1080/10426507.2017.1292273","url":null,"abstract":"GRAPHICAL ABSTRACT ABSTRACT Methyl 3,5-anhydro-3-thiopentofuranosides (“3,5-Thietanopentosides”) of the D-xylo, L-lyxo and 2-deoxy-D-threo series were oxidized to the corresponding S-oxides (sulfoxides) and/or S,S-dioxides (sulfones) by use of hydrogen peroxide or meta-chloroperbenzoic acid. The diastereoisomers resulting from the additional chiral sulfur center in the sulfoxides could be separated. Their configuration was assigned by NMR spectroscopy and in one case unequivocally corroborated by an X-ray structure analysis. The observed stereoselectivity of the oxidation can be attributed to the specific steric requirements in the different thietano sugars. X-Ray structural analyses of three crystalline sulfones were also performed. Attempts to generate carbanions of the sulfoxides and sulfones and to use these for reactions with electrophiles were not successful.","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"26 1","pages":"919 - 928"},"PeriodicalIF":0.0,"publicationDate":"2017-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"83398696","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 : 2017-02-17DOI: 10.1080/10426507.2017.1292272
Zhengbo Han, Wen-Yuan Wu, F. Chen, Xixia Guan, Xiao-Huan Fu, Peng Jiang, Rong Wan
GRAPHICAL ABSTRACT ABSTRACT On the basis of the commercial insecticide Fipronil, a series of novel arylpyrazole derivatives containing the cyhalothroyl thiourea moiety were designed and synthesized via the key intermediate 5-amino-3-cyano-1-(substituted phenyl) pyrazole. The structures of target compounds were characterized by 1H NMR, FT-IR, elemental analysis and single crystal X-ray diffraction analysis. Their insecticidal activities against Culex pipiens and Musca domestica were evaluated. The results of bioassays indicated that title compounds exhibited satisfactory insecticidal activities. Among those, Compound 7t ((E)-3-(2-chloro- 3, 3, 3-trifluoroprop-1-en-1-yl)-N-((3-cyano-1-(2, 6- dichloro-4-(trifluoromethyl) phenyl)-1H-pyrazol-5-yl) carbamothioyl)- 2, 2-dimethyl cyclopropane carboxamide) exhibited the best insecticidal activities because of its lowest KT50 values, which are superior to the commercial insecticide Dextral tetramethrin and similar to Prallethrin. The type and position of substituent on the benzene ring played important roles on the biological activities of target compounds.
{"title":"Design, synthesis, crystal structure and insecticidal evaluation of novel arylpyrazole derivatives containing cyhalothroyl thiourea moiety","authors":"Zhengbo Han, Wen-Yuan Wu, F. Chen, Xixia Guan, Xiao-Huan Fu, Peng Jiang, Rong Wan","doi":"10.1080/10426507.2017.1292272","DOIUrl":"https://doi.org/10.1080/10426507.2017.1292272","url":null,"abstract":"GRAPHICAL ABSTRACT ABSTRACT On the basis of the commercial insecticide Fipronil, a series of novel arylpyrazole derivatives containing the cyhalothroyl thiourea moiety were designed and synthesized via the key intermediate 5-amino-3-cyano-1-(substituted phenyl) pyrazole. The structures of target compounds were characterized by 1H NMR, FT-IR, elemental analysis and single crystal X-ray diffraction analysis. Their insecticidal activities against Culex pipiens and Musca domestica were evaluated. The results of bioassays indicated that title compounds exhibited satisfactory insecticidal activities. Among those, Compound 7t ((E)-3-(2-chloro- 3, 3, 3-trifluoroprop-1-en-1-yl)-N-((3-cyano-1-(2, 6- dichloro-4-(trifluoromethyl) phenyl)-1H-pyrazol-5-yl) carbamothioyl)- 2, 2-dimethyl cyclopropane carboxamide) exhibited the best insecticidal activities because of its lowest KT50 values, which are superior to the commercial insecticide Dextral tetramethrin and similar to Prallethrin. The type and position of substituent on the benzene ring played important roles on the biological activities of target compounds.","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"13 1","pages":"911 - 918"},"PeriodicalIF":0.0,"publicationDate":"2017-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"85298139","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 : 2017-02-01DOI: 10.1080/10426507.2016.1252363
Abdulmajeed S H Alsamarrai
GRAPHICAL ABSTRACT ABSTRACT The present work is intended to provide a process for synthesizing anhydroecgonine derivatives without using cocaine as a starting material. This process involves the synthesis of an anhydroecgonine bearing sulphonyl group instead of carboxylate group at the position C2 for the tropane system, from 7-(p-toluenesulphonyl)cyclohepta-2,4,6-triene and a variety of amines.
{"title":"Synthesis of 2-(p-toluenesulphonyl) tropane-2-ene: Anhydroecgonine analog","authors":"Abdulmajeed S H Alsamarrai","doi":"10.1080/10426507.2016.1252363","DOIUrl":"https://doi.org/10.1080/10426507.2016.1252363","url":null,"abstract":"GRAPHICAL ABSTRACT ABSTRACT The present work is intended to provide a process for synthesizing anhydroecgonine derivatives without using cocaine as a starting material. This process involves the synthesis of an anhydroecgonine bearing sulphonyl group instead of carboxylate group at the position C2 for the tropane system, from 7-(p-toluenesulphonyl)cyclohepta-2,4,6-triene and a variety of amines.","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"105 1","pages":"252 - 254"},"PeriodicalIF":0.0,"publicationDate":"2017-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"80660589","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 : 2017-02-01DOI: 10.1080/10426507.2016.1250761
R. Glass, K. Char, J. Pyun
GRAPHICAL ABSTRACT ABSTRACT Copolymerization of liquid sulfur with 1,3-di-isopropenylbenzene in the absence of any organic solvent provides a stable copolymer which can be cast in molds and also forms a transparent glass. This new plastic has been found to be an advantageous component of lithium-sulfur batteries and can be processed into lenses with a high refractive index and suitable for IR thermal imaging. These polymers are also shown to be “self-healing.” That is, scratched and now opaque lenses can be repaired simply by thermal treatment. Polymerization of sulfur with 1,4-diphenylbutadiyne provides stable polymers with thiophene sulfur linkages which are improved cathode materials for lithium-sulfur batteries. Studies delineating the chemistry behind these remarkable results and characterization of these materials has been explored.
{"title":"From waste to valuable plastics–Discovery of new paradigms from well-studied systems with elemental sulfur","authors":"R. Glass, K. Char, J. Pyun","doi":"10.1080/10426507.2016.1250761","DOIUrl":"https://doi.org/10.1080/10426507.2016.1250761","url":null,"abstract":"GRAPHICAL ABSTRACT ABSTRACT Copolymerization of liquid sulfur with 1,3-di-isopropenylbenzene in the absence of any organic solvent provides a stable copolymer which can be cast in molds and also forms a transparent glass. This new plastic has been found to be an advantageous component of lithium-sulfur batteries and can be processed into lenses with a high refractive index and suitable for IR thermal imaging. These polymers are also shown to be “self-healing.” That is, scratched and now opaque lenses can be repaired simply by thermal treatment. Polymerization of sulfur with 1,4-diphenylbutadiyne provides stable polymers with thiophene sulfur linkages which are improved cathode materials for lithium-sulfur batteries. Studies delineating the chemistry behind these remarkable results and characterization of these materials has been explored.","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"3 1","pages":"157 - 161"},"PeriodicalIF":0.0,"publicationDate":"2017-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"91047212","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 : 2017-02-01DOI: 10.1080/10426507.2016.1252370
E. Clennan, Xiaoping Zhang, Toby Petek
GRAPHICAL ABSTRACT ABSTRACT The first examples of chiral helical viologens are reported. These novel compounds have sufficiently long singlet lifetimes to support bimolecular photochemical reactions. They are quenched with diffusion-controlled rates with dialkyl-, diaryl-, and alkyl-aryl sulfides presumably by a charge transfer/electron transfer mechanism.
{"title":"Synthesis, reactivity, and sulfide quenching of helical viologens","authors":"E. Clennan, Xiaoping Zhang, Toby Petek","doi":"10.1080/10426507.2016.1252370","DOIUrl":"https://doi.org/10.1080/10426507.2016.1252370","url":null,"abstract":"GRAPHICAL ABSTRACT ABSTRACT The first examples of chiral helical viologens are reported. These novel compounds have sufficiently long singlet lifetimes to support bimolecular photochemical reactions. They are quenched with diffusion-controlled rates with dialkyl-, diaryl-, and alkyl-aryl sulfides presumably by a charge transfer/electron transfer mechanism.","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"146 1","pages":"222 - 226"},"PeriodicalIF":0.0,"publicationDate":"2017-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"76079791","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 : 2017-02-01DOI: 10.1080/10426507.2016.1252367
Róża Hamera-Fałdyga, P. Grzelak, Paulina Pipiak, G. Mlostoń
GRAPHICAL ABSTRACT ABSTRACT The goal of the present study was elaboration of an efficient and simple protocol for the preparation of hetaryl and ferrocenyl functionalized thioketones via treatment of the corresponding ketones with Lawesson's reagent (L.R.) under microwave irradiation (M.W.). The application of microwaves reduces the reaction time and in most cases leads to the improvement of yields of isolated, pure thioketones.
{"title":"Microwave assisted synthesis of ferrocenyl and hetaryl functionalized thioketones","authors":"Róża Hamera-Fałdyga, P. Grzelak, Paulina Pipiak, G. Mlostoń","doi":"10.1080/10426507.2016.1252367","DOIUrl":"https://doi.org/10.1080/10426507.2016.1252367","url":null,"abstract":"GRAPHICAL ABSTRACT ABSTRACT The goal of the present study was elaboration of an efficient and simple protocol for the preparation of hetaryl and ferrocenyl functionalized thioketones via treatment of the corresponding ketones with Lawesson's reagent (L.R.) under microwave irradiation (M.W.). The application of microwaves reduces the reaction time and in most cases leads to the improvement of yields of isolated, pure thioketones.","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"23 1","pages":"197 - 198"},"PeriodicalIF":0.0,"publicationDate":"2017-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"83298336","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 : 2017-02-01DOI: 10.1080/10426507.2016.1259237
M. A. Althoff, A. Bertsch, M. Metzulat, O. Kalthoff, K. Karaghiosoff
GRAPHICAL ABSTRACT ABSTRACT Detection and analysis of organophosphates has long been a challenge to numerous researchers and first responders in the field. Presented is a study of nine organo(thio)phosphates closely related to the Chemical Weapons Convention which were investigated with IR, NMR, GC-MS, and HPLC-ESI-MS techniques. The results obtained show some interesting features regarding the easy differentiation between the different isomers, as well as proves the toxicity of the molecules by use of Dräger® test tubes.
{"title":"New aspects of the detection and analysis of organo(thio)phosphates related to the chemical weapons convention","authors":"M. A. Althoff, A. Bertsch, M. Metzulat, O. Kalthoff, K. Karaghiosoff","doi":"10.1080/10426507.2016.1259237","DOIUrl":"https://doi.org/10.1080/10426507.2016.1259237","url":null,"abstract":"GRAPHICAL ABSTRACT ABSTRACT Detection and analysis of organophosphates has long been a challenge to numerous researchers and first responders in the field. Presented is a study of nine organo(thio)phosphates closely related to the Chemical Weapons Convention which were investigated with IR, NMR, GC-MS, and HPLC-ESI-MS techniques. The results obtained show some interesting features regarding the easy differentiation between the different isomers, as well as proves the toxicity of the molecules by use of Dräger® test tubes.","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"2017 1","pages":"149 - 156"},"PeriodicalIF":0.0,"publicationDate":"2017-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"86771886","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 : 2017-02-01DOI: 10.1080/10426507.2016.1255621
Thomas Castanheiro, J. Suffert, Morgan Donnard, M. Gulea
GRAPHICAL ABSTRACT ABSTRACT Two methodologies to access S-heterocycles and mixed N,S-heterocycles via metal-mediated domino reactions are described. One involves a cyclocarbopalladation/cross-coupling domino process and leads to benzene-fused five- or six-membered sulfur heterocycles with a stereo defined tetrasubstituted exocyclic double bond. The other consists in a three-component domino reaction between 2-aminophenyl disulfide, copper cyanide, and an electrophile to access N-substituted 2-amino benzothiazoles. Preliminary results in the use of the second method to access N-substituted 2-imino benzothiazoles are also reported.
摘要描述了两种通过金属介导的多米诺反应获得s -杂环和混合N, s -杂环的方法。一种涉及环碳杂化/交叉偶联多米诺骨牌过程，导致苯融合的五元或六元硫杂环具有立体定义的四取代外环双键。另一种是2-氨基苯基二硫化物、氰化铜和亲电试剂之间的三组分多米诺骨牌反应，以获得n取代的2-氨基苯并噻唑。本文还报道了用第二种方法获得n -取代2-亚氨基苯并噻唑的初步结果。
{"title":"Synthesis of sulfur heterocycles via domino metal-mediated reactions","authors":"Thomas Castanheiro, J. Suffert, Morgan Donnard, M. Gulea","doi":"10.1080/10426507.2016.1255621","DOIUrl":"https://doi.org/10.1080/10426507.2016.1255621","url":null,"abstract":"GRAPHICAL ABSTRACT ABSTRACT Two methodologies to access S-heterocycles and mixed N,S-heterocycles via metal-mediated domino reactions are described. One involves a cyclocarbopalladation/cross-coupling domino process and leads to benzene-fused five- or six-membered sulfur heterocycles with a stereo defined tetrasubstituted exocyclic double bond. The other consists in a three-component domino reaction between 2-aminophenyl disulfide, copper cyanide, and an electrophile to access N-substituted 2-amino benzothiazoles. Preliminary results in the use of the second method to access N-substituted 2-imino benzothiazoles are also reported.","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"17 1","pages":"162 - 165"},"PeriodicalIF":0.0,"publicationDate":"2017-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"74793983","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 : 2017-02-01DOI: 10.1080/10426507.2016.1255622
M. Stefaniak, J. Romański
GRAPHICAL ABSTRACT ABSTRACT The efficient synthesis of new macrocyclic systems via nucleophilic ring opening reaction of epoxides by thiols was described. Initially new macrocyclic compounds were obtained as a mixture of diastereomers. Preparative thin layer chromatography was applied to separate meso and pairs of enantiomer. The identification of products using a chiral HPLC column and mass spectroscopy was utilized.
{"title":"Application of HPLC for the screening of separation of new macrocyclic systems","authors":"M. Stefaniak, J. Romański","doi":"10.1080/10426507.2016.1255622","DOIUrl":"https://doi.org/10.1080/10426507.2016.1255622","url":null,"abstract":"GRAPHICAL ABSTRACT ABSTRACT The efficient synthesis of new macrocyclic systems via nucleophilic ring opening reaction of epoxides by thiols was described. Initially new macrocyclic compounds were obtained as a mixture of diastereomers. Preparative thin layer chromatography was applied to separate meso and pairs of enantiomer. The identification of products using a chiral HPLC column and mass spectroscopy was utilized.","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"142 1","pages":"245 - 248"},"PeriodicalIF":0.0,"publicationDate":"2017-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"82728147","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 : 2017-02-01DOI: 10.1080/10426507.2016.1269231
M. Ahmadian-Moghaddam, A. Bekhradnia, Monire Tatar
GRAPHICAL ABSTRACT ABSTRACT A series of new N-acetyl/thioacetyl-(E)-stilbene benzenesulfonamide derivatives were synthesized regioselectively in moderate to high yields by following a convenient, three-step procedure. The procedure consists of the direct oxidative conversion of a thiol compound to the corresponding sulfonyl chloride using TMSCl/KNO3, followed by a room temperature reaction in a one-pot transformation of the resultant sulfonyl chloride into N-acetyl/thioacetyl sulfonamide, which undergoes a further Pd-catalyzed coupling reaction, giving rise to the stilbene compounds reported for the first time.
{"title":"A facile method for regioselective synthesis of new N-acetyl/thioacetyl-(E)-stilbene benzenesulfonamide derivatives via N-acetyl/thioacetyl sulfonamide formation","authors":"M. Ahmadian-Moghaddam, A. Bekhradnia, Monire Tatar","doi":"10.1080/10426507.2016.1269231","DOIUrl":"https://doi.org/10.1080/10426507.2016.1269231","url":null,"abstract":"GRAPHICAL ABSTRACT ABSTRACT A series of new N-acetyl/thioacetyl-(E)-stilbene benzenesulfonamide derivatives were synthesized regioselectively in moderate to high yields by following a convenient, three-step procedure. The procedure consists of the direct oxidative conversion of a thiol compound to the corresponding sulfonyl chloride using TMSCl/KNO3, followed by a room temperature reaction in a one-pot transformation of the resultant sulfonyl chloride into N-acetyl/thioacetyl sulfonamide, which undergoes a further Pd-catalyzed coupling reaction, giving rise to the stilbene compounds reported for the first time.","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"38-40 1","pages":"481 - 484"},"PeriodicalIF":0.0,"publicationDate":"2017-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"78287976","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}
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