Patrycja Ledwoń, Michał Jewginski, Claudia Bello, Francesca Nuti, Paolo Rovero, Rafal Latajka, Anna Maria Papini
The Front Cover shows a set of Safirinium-dye derivatives used for the facile preparation of peptide conjugates as potential elastase inhibitors, by exploiting a lysine side chain as an effective linker between the dye and the peptide. With an optimized peptide sequence forming the core and triazolium derivatives acting as particular caps, we can create molecular tools capable of tuning the activity of a selected enzyme. Details of this approach are reported in the Research Article by R. Latajka, A. M. Papini and co-workers (DOI: 10.1002/ejoc.202400399). Structure taken from PDB ID: 1QR3.
封面显示的是一组萨菲鎓染料衍生物，通过利用赖氨酸侧链作为染料和肽之间的有效连接物，用于轻松制备肽共轭物，作为潜在的弹性蛋白酶抑制剂。有了构成核心的优化肽序列和作为特殊盖帽的三唑鎓衍生物，我们就能创造出能够调节选定酶活性的分子工具。R. Latajka、A. M. Papini 及合作者的研究文章中报告了这一方法的细节。Papini 及其合作者的研究文章中（DOI: 10.1002/ejoc.202400399）。结构取自 PDB ID：1QR3。
{"title":"Front Cover: Synthetic Strategies to Prepare Bioactive Lysine and Peptide Conjugates With Triazolium Derivatives (Eur. J. Org. Chem. 38/2024)","authors":"Patrycja Ledwoń, Michał Jewginski, Claudia Bello, Francesca Nuti, Paolo Rovero, Rafal Latajka, Anna Maria Papini","doi":"10.1002/ejoc.202483801","DOIUrl":"10.1002/ejoc.202483801","url":null,"abstract":"<p><b>The Front Cover</b> shows a set of <i>Safirinium</i>-dye derivatives used for the facile preparation of peptide conjugates as potential elastase inhibitors, by exploiting a lysine side chain as an effective linker between the dye and the peptide. With an optimized peptide sequence forming the core and triazolium derivatives acting as particular caps, we can create molecular tools capable of tuning the activity of a selected enzyme. Details of this approach are reported in the Research Article by R. Latajka, A. M. Papini and co-workers (DOI: 10.1002/ejoc.202400399). Structure taken from PDB ID: 1QR3.\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure>\u0000 </p>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"27 38","pages":""},"PeriodicalIF":2.5,"publicationDate":"2024-10-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202483801","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142415612","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Santhosh Kumar Alla, Kotari Shakeena, Bokka Srinivas, Thammana Subha Sai Sriram, Leela Prasad Chamanthula, Kiran Indukuri, Muthyala Murali Krishna Kumar
A metal-free, 4,5-difluoro-2-iodobenzoic acid-catalyzed C–H functionalization strategy is developed for the synthesis of 2-(hetero)aryl benzothiazoles from aryl isothiocyanates and unfunctionalized arenes/thiophenes/furans at room temperature. The procedure entails a one-pot, cascade carbon–carbon and carbon–sulfur bond formation facilitated by triflic acid, which serves as both a Bronsted acid and a ligand source at the in situ generated I(III) centre. This process is atom-economical and offers benefits over existing protocols for synthesizing benzothiazoles in terms of ease of use, eco-friendliness, and not requiring the typical use of aryl aldehyde/carboxylic acid precursors. Mechanistic studies were carried out, and the synthetic utility of the protocol was demonstrated for the synthesis of the benzothiazole-based antitumor drug GW-610.
{"title":"Hypervalent Iodine Catalyzed Cascade C–H Functionalization: An Atom-Economical Strategy to Access Diverse 2-Substituted Benzothiazoles","authors":"Santhosh Kumar Alla, Kotari Shakeena, Bokka Srinivas, Thammana Subha Sai Sriram, Leela Prasad Chamanthula, Kiran Indukuri, Muthyala Murali Krishna Kumar","doi":"10.1002/ejoc.202401043","DOIUrl":"https://doi.org/10.1002/ejoc.202401043","url":null,"abstract":"A metal-free, 4,5-difluoro-2-iodobenzoic acid-catalyzed C–H functionalization strategy is developed for the synthesis of 2-(hetero)aryl benzothiazoles from aryl isothiocyanates and unfunctionalized arenes/thiophenes/furans at room temperature. The procedure entails a one-pot, cascade carbon–carbon and carbon–sulfur bond formation facilitated by triflic acid, which serves as both a Bronsted acid and a ligand source at the in situ generated I(III) centre. This process is atom-economical and offers benefits over existing protocols for synthesizing benzothiazoles in terms of ease of use, eco-friendliness, and not requiring the typical use of aryl aldehyde/carboxylic acid precursors. Mechanistic studies were carried out, and the synthetic utility of the protocol was demonstrated for the synthesis of the benzothiazole-based antitumor drug GW-610.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"8 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142398556","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Lewan Li, Mengxiang Luo, Shuntian Liu, Jian Lv, Jie Zeng, Qiongjiao Yan, Jie Liao, Haifeng Wang, Shuangxi Gu
Rapid and efficient construction of α‐haloketones with diazo compounds and amidine·HX (X = Cl, Br, I) salts as halogen sources has been recognized as a simple and practical strategy. The reaction exhibits a broad scope and scalability, thereby enabling synthesis of a broad spectrum of functionally orchestrated α‐haloketones under mild and metal‐free conditions in a short time. Control experiments established the involvement of triffate 11 in the mechanism
{"title":"Rapid and General Access to α‐Halogenated Carbonyl Compounds Using Amidine Halide Salts as Halogen Sources under Mild Conditions","authors":"Lewan Li, Mengxiang Luo, Shuntian Liu, Jian Lv, Jie Zeng, Qiongjiao Yan, Jie Liao, Haifeng Wang, Shuangxi Gu","doi":"10.1002/ejoc.202401111","DOIUrl":"https://doi.org/10.1002/ejoc.202401111","url":null,"abstract":"Rapid and efficient construction of α‐haloketones with diazo compounds and amidine·HX (X = Cl, Br, I) salts as halogen sources has been recognized as a simple and practical strategy. The reaction exhibits a broad scope and scalability, thereby enabling synthesis of a broad spectrum of functionally orchestrated α‐haloketones under mild and metal‐free conditions in a short time. Control experiments established the involvement of triffate 11 in the mechanism","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"83 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142397774","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Abstract: A series of semi-saturated fused polycyclic iminosugars were synthesized by one-pot stereoselective three-component reactions of D-ribose tosylate, aniline and cycloenones under heating conditions. The N-aryl enamine derived from an iminium ion is the key intermediate for the reaction. In this way, various novel complex fused iminosugars were obtained through a normal Diels-Alder mechanism at 80 °C. This strategy will enable the preparation of bioactive iminosugar analogues with structural diversity.
摘要：在加热条件下，通过 D-核糖对甲苯磺酸盐、苯胺和环烯酮的单锅立体选择性三组分反应合成了一系列半饱和融合多环亚氨基糖。由亚胺离子衍生的 N-芳基烯胺是反应的关键中间体。通过这种方法，在 80 °C 下通过正常的 Diels-Alder 机理获得了各种新型复合融合亚氨基糖。这种策略将有助于制备具有结构多样性的生物活性亚氨基糖类似物。
{"title":"One-Pot Synthesis of Semisaturated Fused Polycyclic Iminosugars by a Diels-Alder Reaction","authors":"Song Xie, jilai Wu, Likai Zhou, Chao Wei, Xiaoliu Li, Hua Chen","doi":"10.1002/ejoc.202401005","DOIUrl":"https://doi.org/10.1002/ejoc.202401005","url":null,"abstract":"Abstract: A series of semi-saturated fused polycyclic iminosugars were synthesized by one-pot stereoselective three-component reactions of D-ribose tosylate, aniline and cycloenones under heating conditions. The N-aryl enamine derived from an iminium ion is the key intermediate for the reaction. In this way, various novel complex fused iminosugars were obtained through a normal Diels-Alder mechanism at 80 °C. This strategy will enable the preparation of bioactive iminosugar analogues with structural diversity.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"79 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142398341","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
We summarized a strategy for C–H functionalization of cubanes, highlighting recent progress in the field. Cubane, known as a bioisostere of benzene ring, and its functionalization hold significant potential for future drug development. However, owing to its highly strained and thermodynamically unstable nature, the methodologies are limited and their precise and diverse functionalization is challenging in current organic chemistry. In this Concept, we categorized and explained these methodologies, which represents a majority of current cubane C–H functionalization. In addition, we discussed recent advancements in catalytic C–H functionalization methods, demonstrating their potential to address these challenges effectively.
{"title":"Strategy for C–H Functionalization of Cubanes: From Stoichiometric Reaction to Catalytic Methodology","authors":"Masaki Hosaka, Shota Nagasawa, Yoshiharu Iwabuchi","doi":"10.1002/ejoc.202401055","DOIUrl":"https://doi.org/10.1002/ejoc.202401055","url":null,"abstract":"We summarized a strategy for C–H functionalization of cubanes, highlighting recent progress in the field. Cubane, known as a bioisostere of benzene ring, and its functionalization hold significant potential for future drug development. However, owing to its highly strained and thermodynamically unstable nature, the methodologies are limited and their precise and diverse functionalization is challenging in current organic chemistry. In this Concept, we categorized and explained these methodologies, which represents a majority of current cubane C–H functionalization. In addition, we discussed recent advancements in catalytic C–H functionalization methods, demonstrating their potential to address these challenges effectively.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"108 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142397853","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Stepan N. Ostarkov, Yana I. Lichtenstein, Yulia A. Antonova, Yulia V. Nelyubina, Vladislav K. Lesnikov, Andrey Tabolin
Reactions of 5,6-dihydro-4H-1,2-oxazine N-oxides with enol diazoacetates were studied. A particular reaction path depends on the amount of catalyst and the order of the addition of the substrates. Use of Rh2(Oct)4 (2 mol.%) leads to chemoselective [3+3]-annulation producing 1,2-oxazine-fused 1,2-oxazine derivatives. With lower catalyst loadings (0.03 mol.%) enol diazoacetates are converted to cyclopropene derivatives, which in situ react with 1,2-oxazine N-oxides via tandem [3+2]-cycloaddition-rearrangement producing oxazine-fused aziridines. Both transformations showed a wide substrate scope and produced target products with good yields and diastereoselectivity, thus allowing selective preparation of these rare heterocyclic systems. A mechanistic rationale for observed chemo- and stereo- selectivities was proposed.
{"title":"Divergent Annulations of 5,6-Dihydro-4H-1,2-Oxazine N-Oxides and Enol Diazoacetates for the Switchable Chemoselective Synthesis of Fused 1,2-Oxazine Derivatives","authors":"Stepan N. Ostarkov, Yana I. Lichtenstein, Yulia A. Antonova, Yulia V. Nelyubina, Vladislav K. Lesnikov, Andrey Tabolin","doi":"10.1002/ejoc.202400768","DOIUrl":"https://doi.org/10.1002/ejoc.202400768","url":null,"abstract":"Reactions of 5,6-dihydro-4H-1,2-oxazine N-oxides with enol diazoacetates were studied. A particular reaction path depends on the amount of catalyst and the order of the addition of the substrates. Use of Rh2(Oct)4 (2 mol.%) leads to chemoselective [3+3]-annulation producing 1,2-oxazine-fused 1,2-oxazine derivatives. With lower catalyst loadings (0.03 mol.%) enol diazoacetates are converted to cyclopropene derivatives, which in situ react with 1,2-oxazine N-oxides via tandem [3+2]-cycloaddition-rearrangement producing oxazine-fused aziridines. Both transformations showed a wide substrate scope and produced target products with good yields and diastereoselectivity, thus allowing selective preparation of these rare heterocyclic systems. A mechanistic rationale for observed chemo- and stereo- selectivities was proposed.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"1 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142385453","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Since the report of oxamide ligands, they have been widely used for the efficient construction of various types of C-X (such as C, N, O and S) bonds. To evaluate whether the easily tunable electronic properties and unique coordination modes of oxamide ligands can also shine in the field of oxidation, we initiated a study on oxamide ligand/copper/air oxidation and applied it to the oxidation of alcohols to assess its practicality and potential applications. The practicality of this strategy was further verified through scale-up reactions on a 100 mmol scale and gram-scale derivatization of pharmaceutical molecules.
{"title":"A new CuI/oxalamide catalytic system for the large-scale aerobic oxidation of alcohols","authors":"Kexue Xing, Jicong Xiang, Zijin Luo, Guiyuan Liu, Xianghao Zhang, Guofu Zhang, Chengrong Ding","doi":"10.1002/ejoc.202400804","DOIUrl":"https://doi.org/10.1002/ejoc.202400804","url":null,"abstract":"Since the report of oxamide ligands, they have been widely used for the efficient construction of various types of C-X (such as C, N, O and S) bonds. To evaluate whether the easily tunable electronic properties and unique coordination modes of oxamide ligands can also shine in the field of oxidation, we initiated a study on oxamide ligand/copper/air oxidation and applied it to the oxidation of alcohols to assess its practicality and potential applications. The practicality of this strategy was further verified through scale-up reactions on a 100 mmol scale and gram-scale derivatization of pharmaceutical molecules.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"29 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142385454","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Honoka Hanashiro, Yuta Ito, Yasufumi Fuchi, Yoshiyuki Hari
This article presents the synthesis and properties of oligonucleotides containing 8,1′‐ethano‐2′‐deoxyadenosine (ethano‐dA) in which the adenine base (ethA) is fixed to the syn conformation. Ethano‐dA phosphoramidite was synthesized by using a 1,5‐hydrogen‐atom transfer/radical cyclization process and introduced into oligonucleotides, which were successfully obtained by employing the 4,4′‐dimethoxytrityl‐off synthesis mode. The duplex‐forming ability of the oligonucleotides containing ethano‐dA was evaluated. In the antiparallel Watson–Crick duplex, the ethA formed stable base pairs with thymine and guanine, in which two Hoogsteen‐type hydrogen bonds could be formed. By contrast, the parallel Hoogsteen duplex containing the ethA:thymine base pair showed thermal stability comparable to that containing a natural adenine:thymine base pair because ethA and thymine can form two Watson–Crick‐type hydrogen bonds. These results indicated that ethano‐dA may be helpful for elucidating the function of adenine bases via the syn conformation in DNA.
{"title":"Oligonucleotides Containing 8,1′‐Ethano‐2′‐deoxyadenosine: Synthesis and Properties","authors":"Honoka Hanashiro, Yuta Ito, Yasufumi Fuchi, Yoshiyuki Hari","doi":"10.1002/ejoc.202400849","DOIUrl":"https://doi.org/10.1002/ejoc.202400849","url":null,"abstract":"This article presents the synthesis and properties of oligonucleotides containing 8,1′‐ethano‐2′‐deoxyadenosine (ethano‐dA) in which the adenine base (ethA) is fixed to the syn conformation. Ethano‐dA phosphoramidite was synthesized by using a 1,5‐hydrogen‐atom transfer/radical cyclization process and introduced into oligonucleotides, which were successfully obtained by employing the 4,4′‐dimethoxytrityl‐off synthesis mode. The duplex‐forming ability of the oligonucleotides containing ethano‐dA was evaluated. In the antiparallel Watson–Crick duplex, the ethA formed stable base pairs with thymine and guanine, in which two Hoogsteen‐type hydrogen bonds could be formed. By contrast, the parallel Hoogsteen duplex containing the ethA:thymine base pair showed thermal stability comparable to that containing a natural adenine:thymine base pair because ethA and thymine can form two Watson–Crick‐type hydrogen bonds. These results indicated that ethano‐dA may be helpful for elucidating the function of adenine bases via the syn conformation in DNA.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"1 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142384383","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Bo Qin, Jie Wang, Xiaojing Wu, Hongyan Cai, Hang Li, Pizheng Zhang
A network-structured supramolecular gel is constructed through host-guest interactions between conjugated ligands and metal ions, leading to enhanced mechanical properties and excellent electrical conductivity. This overcomes the problem of insufficient conductance due to the presence of solvent in the interstitial region of the supramolecular gel. Supramolecular gels can undergo reversible sol-gel transitions by controlling the pH or temperature of the system. In addition, a method has been developed to determine the specific binding ratio of host-guest molecules by conductivity tests, and has been used to verify the specific binding ratio of crown ether to potassium ions. To explain the high conductivity of supramolecular metallic gels, DFT and SEM have been employed to elucidate their conductivity mechanism.
通过共轭配体和金属离子之间的主客体相互作用，构建了一种网络结构的超分子凝胶，从而增强了机械性能和优异的导电性。这克服了由于超分子凝胶间隙区存在溶剂而导致导电性不足的问题。通过控制体系的 pH 值或温度，超分子凝胶可发生可逆的溶胶-凝胶转变。此外，还开发了一种通过电导测试确定主客分子特定结合率的方法，并已用于验证冠醚与钾离子的特定结合率。为了解释超分子金属凝胶的高导电性，采用了 DFT 和 SEM 来阐明其导电机制。
{"title":"A Supramolecular Gel that Exhibits Multi-stimuli Responsiveness and High Conductivity Through Host-Guest Interactions","authors":"Bo Qin, Jie Wang, Xiaojing Wu, Hongyan Cai, Hang Li, Pizheng Zhang","doi":"10.1002/ejoc.202400726","DOIUrl":"https://doi.org/10.1002/ejoc.202400726","url":null,"abstract":"A network-structured supramolecular gel is constructed through host-guest interactions between conjugated ligands and metal ions, leading to enhanced mechanical properties and excellent electrical conductivity. This overcomes the problem of insufficient conductance due to the presence of solvent in the interstitial region of the supramolecular gel. Supramolecular gels can undergo reversible sol-gel transitions by controlling the pH or temperature of the system. In addition, a method has been developed to determine the specific binding ratio of host-guest molecules by conductivity tests, and has been used to verify the specific binding ratio of crown ether to potassium ions. To explain the high conductivity of supramolecular metallic gels, DFT and SEM have been employed to elucidate their conductivity mechanism.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"10 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142384660","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The Front Cover illustrates the SN2-like ring-opening reactions of THF derivatives with the chalcogen elements O, S, Se and Te on both Si(001) and Ge(001) surfaces. The periodic table at the back embodies the trends presented in the work. On the left, the deformation density of the first NOCV in the THF precursor structure showcases the charge transfer towards the surface. The across-trench product of the tellurium derivative is shown on the right. The center features the across-trench transition state geometry of THSe with a deformation density indicating an SN2-like reaction. More information can be found in the Research Article by R. Tonner-Zech and co-workers (DOI: 10.1002/ejoc.202400560).
{"title":"Front Cover: Trends in the Reactivity of Pentacyclic Ether Derivatives on Silicon and Germanium Surfaces Revealed by Energy Decomposition Analysis for Extended Systems (Eur. J. Org. Chem. 37/2024)","authors":"Franz Thiemann, Hendrik Weiske, Ralf Tonner-Zech","doi":"10.1002/ejoc.202483701","DOIUrl":"10.1002/ejoc.202483701","url":null,"abstract":"<p><b>The Front Cover</b> illustrates the S<sub>N</sub>2-like ring-opening reactions of THF derivatives with the chalcogen elements O, S, Se and Te on both Si(001) and Ge(001) surfaces. The periodic table at the back embodies the trends presented in the work. On the left, the deformation density of the first NOCV in the THF precursor structure showcases the charge transfer towards the surface. The across-trench product of the tellurium derivative is shown on the right. The center features the across-trench transition state geometry of THSe with a deformation density indicating an S<sub>N</sub>2-like reaction. More information can be found in the Research Article by R. Tonner-Zech and co-workers (DOI: 10.1002/ejoc.202400560).\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure>\u0000 </p>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"27 37","pages":""},"PeriodicalIF":2.5,"publicationDate":"2024-10-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202483701","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142374408","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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