A. B. Koldobskii, O. S. Shilova, A. A. Druzina, O. I. Artyushin
{"title":"Preparative scalable method for the synthesis of cyclic and acyclic acetals of chloropropiolaldehyde and their transformation into acetals of lithiumpropiolaldehyde","authors":"A. B. Koldobskii, O. S. Shilova, A. A. Druzina, O. I. Artyushin","doi":"10.1007/s11172-024-4428-y","DOIUrl":"10.1007/s11172-024-4428-y","url":null,"abstract":"<div><p>A simple two-step and easily scalable method for the synthesis of cyclic and acyclic acetals of chloropropiolaldehyde was developed. They readily reacted with <i>n</i>-butyllithium to give stable crystalline acetals of lithiumpropiolaldehyde, which, being strong nucleophiles, reacted with chlorotrimethylsilane, chlorotrimethylstannane, and methyl chloroformate to form bifunctional acetylenes in high yields.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 10","pages":"3099 - 3103"},"PeriodicalIF":1.7,"publicationDate":"2024-12-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142778138","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Yu. N. Bubnov, A. A. Prishchenko, M. V. Livantsov, O. P. Novikova, L. I. Livantsova, S. V. Baranin
{"title":"Synthesis of functionalized N-acylated amino acids containing 3- and 4-coordinated phosphorus moieties","authors":"Yu. N. Bubnov, A. A. Prishchenko, M. V. Livantsov, O. P. Novikova, L. I. Livantsova, S. V. Baranin","doi":"10.1007/s11172-024-4417-1","DOIUrl":"10.1007/s11172-024-4417-1","url":null,"abstract":"<div><p>A convenient synthesis of functionalized <i>N</i>-acylated amino acids containing 3- and 4-coordinated phosphorus moieties as well as <i>N</i>-alkoxycarbonyl groups has been developed. Aminomethylation of tricoordinated phosphorus acid esters with <i>N</i>-chloromethylsubstituted <i>N</i>-alkoxycarbonylamino acids proceeds under mild conditions and affords new types of target products of different structures. The resulting compounds are of interest as promising biologically active substances, effective extractants, and water-soluble polydentate ligands.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 10","pages":"3012 - 3026"},"PeriodicalIF":1.7,"publicationDate":"2024-12-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142778486","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
E. V. Balagurova, A. P. Tyurin, I. A. Godovikov, F. M. Dolgushin, I. T. Chizhevsky
{"title":"Synthesis of 11-vertex cobalt bis(diphenylphosphine) complexes based on medium-size non-icosahedral carborane 5,6-nido-C2B8H12. Molecular structure of complex [1,1-{κ2-1′,2′-Ph2P(CH2)2PPh2}-1-H-isonido-1,2,4-CoC2B8H10]","authors":"E. V. Balagurova, A. P. Tyurin, I. A. Godovikov, F. M. Dolgushin, I. T. Chizhevsky","doi":"10.1007/s11172-024-4406-4","DOIUrl":"10.1007/s11172-024-4406-4","url":null,"abstract":"<div><p>The reactions of suspensions of the freshly prepared complexes [Ph<sub>2</sub>P(CH<sub>2</sub>)<sub><i>n</i></sub>PPh<sub>2</sub>] CoCl<sub>2</sub> (<i>n</i> = 2 (dppeCoCl<sub>2</sub>), <i>n</i> = 3 (dpppCoCl<sub>2</sub>), <i>n</i> = 4 (dppbCoCl<sub>2</sub>); dppe is bis(diphenylphosphino)ethane, dppp is 1,3-bis(diphenylphosphino)propane, dppb is 1,4-bis-(diphenylphosphino)butane) with the salts [Na][R<sub>2</sub>C<sub>2</sub>B<sub>8</sub>H<sub>9</sub>] (R = H, Ph), which were obtained <i>in situ</i> by the treatment of carboranes 5,6-<i>nido</i>-R<sub>2</sub>C<sub>2</sub>B<sub>8</sub>H<sub>10</sub> (R = H (<b>1a</b>), Ph (<b>1b</b>)) with NaH in THF at room temperature, afforded 18-electron cobaltahydridocarboranes with <i>isonido</i> structures, [1,1-{κ<sup>2</sup>-Ph<sub>2</sub>P(CH<sub>2</sub>)<sub><i>n</i></sub>PPh<sub>2</sub>}-1-H-<i>isonido</i>-1,2,4-CoR<sub>2</sub>C<sub>2</sub>B<sub>8</sub>H<sub>8</sub>] (R = H, <i>n</i> = 2 (<b>2a</b>), 3 (<b>2b</b>), 4 (<b>2c</b>); R = Ph, <i>n</i> = 2 (<b>2d</b>)). The treatment of <i>nido</i>-carborane <b>1a</b> with potassium hydroxide followed by the addition of [Ph<sub>2</sub>P(CH<sub>2</sub>)<sub><i>n</i></sub>PPh<sub>2</sub>]CoCl<sub>2</sub> (<i>n</i> = 2–4) in ethanol at 20 °C resulted in the formation of ethoxy-substituted complexes [1,1-{κ<sup>2</sup>-Ph<sub>2</sub>P(CH<sub>2</sub>)<sub><i>n</i></sub>PPh<sub>2</sub>}-1-H-3-(EtO)-<i>isonido</i>-1,2,4-CoC<sub>2</sub>B<sub>8</sub>H<sub>9</sub>] (<b>3a–c</b>, <i>n</i> = 2–4) apart from compounds <b>2a–c.</b> All the newly prepared compounds were characterized by a combination of elemental analysis, multinuclear NMR spectroscopy, and IR spectroscopy. The structure of complex <b>2a</b> was studied by X-ray diffraction analysis.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 10","pages":"2890 - 2899"},"PeriodicalIF":1.7,"publicationDate":"2024-12-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142778422","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
O. A. Mikhaylov, M. E. Gurskii, E. Sh. Saigitbatalova, L. Z. Latypova, D. P. Gerasimova, O. A. Lodochnikova, A. R. Kurbangalieva, I. D. Gridnev
{"title":"Allylboration of azole aldehydes: enantioselective synthesis of homoallylic azole alcohols and reconsideration of the mechanism of enantioselectivity","authors":"O. A. Mikhaylov, M. E. Gurskii, E. Sh. Saigitbatalova, L. Z. Latypova, D. P. Gerasimova, O. A. Lodochnikova, A. R. Kurbangalieva, I. D. Gridnev","doi":"10.1007/s11172-024-4408-2","DOIUrl":"10.1007/s11172-024-4408-2","url":null,"abstract":"<div><p>Allylboration of the 1,2,3-triazole and pyrazole aldehydes with triallylborane or 2,4-pentadienyl(dipropyl)borane under mild reaction conditions provides high yields of the corresponding novel homoallylic and dihomoallylic alcohols that can be used to modify the side chain in the triazole- or diazole-based molecules. Enantioselective allylboration of triazole aldehydes with (+)-<i>B</i>-allyldiisopinocampheylborane gave optically active <i>R</i>(+) homoallylic alcohols in good yields with 80–93% <i>ee</i>. The <i>R</i>-configuration of the reaction products was assigned based on the results of DFT calculations and single-crystal X-ray diffraction study. It was demonstrated that, contrary to early theories, stereo-selectivity is controlled by the stabilizing noncovalent interactions rather than intramolecular repulsive ones.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 10","pages":"2910 - 2920"},"PeriodicalIF":1.7,"publicationDate":"2024-12-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142778424","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Theoretical studies of the structure and properties of cyclic hydrogen peroxide clusters: quantum chemical calculations","authors":"S. S. Kiselev, Yu. A. Borisov","doi":"10.1007/s11172-024-4398-0","DOIUrl":"10.1007/s11172-024-4398-0","url":null,"abstract":"<div><p>Density functional theory calculations of the structure and properties of bicyclic and tricyclic hydrogen peroxide (HP) clusters (P<i>n</i>, <i>n</i> = 8–14) in the gas phase were carried out for the first time. Three main types of couplings of two or more ring clusters P4–P7 (tetra-, penta-, hexa-, and heptamer) into a cyclic structure were investigated. The first (type A) includes a reorientation of hydrogen bonds within the cluster and a change in the sign of the dihedral angle (chirality) of several HP molecules, while the second (type B) process entails the formation of bridges comprising two HP molecules, without altering the overall chirality of the cluster. The third type of coupling of two clusters involves the formation of nested structures in which the smaller cluster is located inside the larger one. The thermodynamic parameters of conjugation of clusters P4–P7 with the formation of cyclic structures were calculated. In the gas phase, the heterochiral type A structures have a lower energy than the homochiral type B structures with the same number of HP molecules. In the case of low-energy cyclic clusters, the highest number of hydrogen bonds (2<i>n</i>) is favourable.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 10","pages":"2821 - 2830"},"PeriodicalIF":1.7,"publicationDate":"2024-12-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142778426","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"The use of NiI2 as a catalyst for CO2 addition to oxiranes: activation methods","authors":"S. E. Lyubimov, P. V. Cherkasova","doi":"10.1007/s11172-024-4426-0","DOIUrl":"10.1007/s11172-024-4426-0","url":null,"abstract":"<div><p>Nickel(<span>ii</span>) iodide with organic and inorganic additives was tested in the addition of CO<sub>2</sub> to oxiranes. The introduction of diethylamine leads to the formation of an effective catalyst, which is, in some cases, capable of completing the reaction in the presence of 1 mol.% NiI<sub>2</sub> over a period of 1 h.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 10","pages":"3090 - 3093"},"PeriodicalIF":1.7,"publicationDate":"2024-12-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142778136","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
O. V. Bykhovskaya, I. Yu. Kudryavtsev, T. V. Baulina, M. P. Pasechnik, V. K. Brel
{"title":"Synthesis of non-symmetrical triarylphosphine oxide with fluorophore groups","authors":"O. V. Bykhovskaya, I. Yu. Kudryavtsev, T. V. Baulina, M. P. Pasechnik, V. K. Brel","doi":"10.1007/s11172-024-4418-0","DOIUrl":"10.1007/s11172-024-4418-0","url":null,"abstract":"<div><p>The Mitsunobu reaction of tris(2-hydroxyphenyl)phosphine oxide with <i>N</i>-(3-hydroxypropyl)-4-nitro-1,8-naphthalimide resulted in alkylation of only two phenolic groups. The aromatic nitro groups of the synthesized product were replaced by the BuNH groups by the reaction with butylamine. The synthesized product exhibited fluorophore properties.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 10","pages":"3027 - 3031"},"PeriodicalIF":1.7,"publicationDate":"2024-12-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142778297","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
A. S. Chistyakov, D. A. Knyazev, E. N. Zorina-Tikhonova, M. A. Kiskin, A. V. Vologzhanina, I. L. Eremenko
{"title":"Synthesis and structure of copper(ii) and manganese(ii) diethylmalonates with 4,4′-bipyridine","authors":"A. S. Chistyakov, D. A. Knyazev, E. N. Zorina-Tikhonova, M. A. Kiskin, A. V. Vologzhanina, I. L. Eremenko","doi":"10.1007/s11172-024-4400-x","DOIUrl":"10.1007/s11172-024-4400-x","url":null,"abstract":"<div><p>Two new mixed-ligand 3d-metal (Mn<sup>II</sup>, Cu<sup>II</sup>) coordination compounds with diethylmalonate anions and 4,4′-bipyridine were synthesized and characterized by IR spectroscopy and X-ray diffraction. The complex [Mn(HEt<sub>2</sub>mal)<sub>2</sub>(bpy)(H<sub>2</sub>O)<sub>2</sub>]<sub><i>n</i></sub> (<b>1</b>) (H<sub>2</sub>Et<sub>2</sub>mal is diethylmalonic acid, bpy is 4,4′-bipyridine) contains six-coordinate metal atoms and has a chain structure. In the structure of complex 1, two interpenetrating frameworks are formed through hydrogen bonds. The coordination polymer {[Cu<sub>2</sub>(Et<sub>2</sub>mal)<sub>2</sub>(bpy)(H<sub>2</sub>O)]•6 H<sub>2</sub>O}<sub><i>n</i></sub> (<b>2</b>) contains four- and five-coordinate copper(<span>ii</span>) cations and forms infinite layers perpendicular to the crystallographic axis <i>a</i>.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 10","pages":"2838 - 2843"},"PeriodicalIF":1.7,"publicationDate":"2024-12-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142778428","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
I. K. Rubtsova, M. A. Shmelev, S. A. Nikolaevskii, D. A. Banaru, I. A. Yakushev, P. V. Dorovatovskii, S. M. Aksenov, A. A. Sidorov, I. L. Eremenko, M. A. Kiskin
{"title":"Effect of crystallization conditions on the composition and structure of {ZnCa} metal-organic coordination polymers with isophthalate anions","authors":"I. K. Rubtsova, M. A. Shmelev, S. A. Nikolaevskii, D. A. Banaru, I. A. Yakushev, P. V. Dorovatovskii, S. M. Aksenov, A. A. Sidorov, I. L. Eremenko, M. A. Kiskin","doi":"10.1007/s11172-024-4402-8","DOIUrl":"10.1007/s11172-024-4402-8","url":null,"abstract":"<div><p>The reaction of the heterometallic complex [Zn<sub>2</sub>Ca(piv)<sub>6</sub>(py)<sub>2</sub>] (piv is pivalate anion, py is pyridine) with isophthalic acid (1,3-H<sub>2</sub>bdc) under the solvothermal conditions afforded a series of new {ZnCa} coordination polymers [Zn<sub>2</sub>Ca(DMF)<sub>2</sub>(1,3-bdc)<sub>3</sub>]<sub><i>n</i></sub> • •<i>n</i>(DMF) (<b>1</b>), [Zn<sub>3</sub>Ca<sub>3</sub>(H<sub>2</sub>O)<sub>5</sub>(DMF)(1,3-bdc)<sub>6</sub>]<sub><i>n</i></sub> • 3<i>n</i>(C<sub>6</sub>H<sub>6</sub>) • 3<i>n</i>(DMF) (<b>2</b>), and [Zn<sub>4</sub>Ca<sub>3</sub>(H<sub>2</sub>O)<sub>4</sub>(NMP)(1,3-bdc)<sub>8</sub>]<sub><i>n</i></sub> (<b>3</b>, NMP is <i>N</i>-methylpyrrolidone). The structures of the new compounds were determined by single-crystal X-ray diffraction. Depending on the conditions of the synthesis and crystallization, porous coordination polymers with different structures and composition were obtained. The use of poorly soluble zinc iso-phthalate as one of the starting compounds in the reaction with calcium nitrate enabled the preparation of single-phase complex <b>1</b> in amounts required for further investigations. The synthesized compounds were characterized by single-crystal X-ray diffraction, powder X-ray diffraction, IR spectroscopy, and elemental analysis.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 10","pages":"2852 - 2865"},"PeriodicalIF":1.7,"publicationDate":"2024-12-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142778430","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
V. S. Bochenkov, R. N. Shamsutdinova, A. I. Ryzhkov, V. L. Baklagin, A. Yu. Tsegelskaya, I. G. Abramov, A. I. Buzin, A. A. Kuznetsov
{"title":"Novel thermosetting diimides containing terminal propargyl groups","authors":"V. S. Bochenkov, R. N. Shamsutdinova, A. I. Ryzhkov, V. L. Baklagin, A. Yu. Tsegelskaya, I. G. Abramov, A. I. Buzin, A. A. Kuznetsov","doi":"10.1007/s11172-024-4388-2","DOIUrl":"10.1007/s11172-024-4388-2","url":null,"abstract":"<div><p>A series of new thermosetting diimides containing terminal propargyl groups was synthesized via one-step high-temperature catalytic condensation of dianhydrides of a tetracarboxylic acid with <i>N</i>-Boc-(4-propargyloxy)aniline (APR) in the so-called “active medium”, <i>viz.</i> molten benzoic acid. Structures of the obtained compounds were confirmed by <sup>1</sup>H NMR and IR spectroscopy. The effect of symmetrical and unsymmetrical structures of the middle bis-imide moiety obtained from dianhydrides of isomeric diphenyltetracarboxylic acid on physicochemical characteristics of the diimides was evaluated. A similar comparison of properties was also carried out for a pair of new propargyl-containing diimides synthesized from dianhydrides of symmetric and asymmetric structure: 4,4-biphenylenedioxydiphthalic and 3,4-biphenylenedioxydiphthalic dianhydrides, respectively. Thermal properties of thermosetting oligoimides were estimated using DSC and TMA methods. It was found that their thermal properties and solubility in organic solvents depend significantly on the structure of central bis-imide moiety.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 9","pages":"2750 - 2757"},"PeriodicalIF":1.7,"publicationDate":"2024-10-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142518760","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}