Article
Chemistry, Organic
Lipeng Long, Wenjia Wang, Yuping Zhu, Wenjun Luo, Yi Zhang, Juxiu Chen, Yuting Wei, Zhengwang Chen
Summary: A simple and practical method for the synthesis of phthalimides from readily available maleimide has been developed using triethylamine as a 1,3-diene variant. The reaction can be performed without a metal catalyst and exhibits a high level of functional group tolerance.
Article
Chemistry, Organic
Man Ki Sit, Hui Hui Cao, Yan-Dong Wu, Tsz Chun Yip, Lars Eric Bendel, Wen Zhang, Wei-Min Dai
Summary: The synthesis of C19-truncated maltepolide E was achieved using a diene-ene ring-closing metathesis strategy, while preserving the integrity of the C11-C14 alkenyl epoxy unit. Removal of the C17-OH group resulted in its attack at the C14 position, causing double bond migration and epoxide ring opening to produce C19-truncated maltepolides A and B, which are proposed intermediates in the biosynthesis of maltepolides.
Article
Chemistry, Multidisciplinary
Martin Jaeger Pedersen, Christian Marcus Pedersen
Summary: A method for introducing dimethylphenylsilyl at the 4-position in carbohydrates has been developed, showing higher reactivity compared to the corresponding 4-deoxy-analogue. The introduction of a C-Si increases the relative reactivity by a modest factor of around two.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Jun Yang, Pan Zhang, Zeyuan Shen, Yi Zhou, Zhi-Xiang Yu
Summary: We propose an endo-oxidative cyclometallation (endo-OCM) reaction as a new reaction mode, which can provide a new concept for chemistry and the design of other reactions. We report a Rh(I)-catalyzed intramolecular [4 + 3] cycloaddition reaction, which efficiently synthesizes 5/7-fused bicyclic skeletons with a bridgehead ethyl substituent. Quantum chemical calculations have been carried out to analyze factors affecting the competition of exo-OCM and endo-OCM.
Article
Chemistry, Organic
Julian Klepp, Thomas Bousfield, Hugh Cummins, Sarah V. A-M Legendre, Jason E. Camp, Ben W. Greatrex
Summary: This paper reports a novel aldol/Michael cascade reaction, which involves the reactions of aromatic aldehydes and levoglucosenone promoted by methoxide. The reaction yields bridged alpha,0-unsaturated ketones, with up to 91% yield in 14 examples. The formation of the bridged species is thermodynamically favored, except in the case of 5-methylfurfural and pyrrole-2-carboxaldehyde.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Haiping Yang, Shuaishuai Lei, Kun Xu, Yang Fang, Xu Chen, Yingquan Chen, Xianhua Wang, Hanping Chen
Summary: The study found that under the catalytic action of sulfonated carbon, the optimal conditions for producing LGO were a temperature of 400 ℃ and a mass ratio of 1:1.
FUEL PROCESSING TECHNOLOGY
(2022)
Article
Agricultural Engineering
Bo Wang, Kai Li, Cheng-bo Zhang, Bin Hu, Yan-qin Huang, Ti-peng Wang, Qiang Lu
Summary: This study aimed to improve the production efficiency of levoglucosenone (LGO) from cellulose catalytic pyrolysis by optimizing its ultrastructure. Cellulose was pretreated with Na2CO3 solutions of different concentrations and Amberlyst-15 (A-15) at different temperatures. The effects of pretreatment on cellulose ultrastructure, particularly the degree of polymerization (DP) and crystallinity index (CrI), were investigated. The catalytic pyrolysis experiments revealed that Na2CO3 pretreatment significantly reduced CrI of cellulose and slightly decreased DP. Low Na2CO3 concentration promoted LGO generation by reducing CrI, while high concentration hindered LGO formation due to the transformation of cellulose I & beta; to II. A-15 pretreatment increased CrI and decreased DP with increasing temperature, leading to a gradual decrease in LGO yield. The cellulose pretreated with 1% Na2CO3 solution exhibited the highest LGO yield of 19.76 wt.%, higher than that of raw cellulose (18.04 wt.%), with lower pyrolysis temperature and catalyst dosage.
INDUSTRIAL CROPS AND PRODUCTS
(2023)
Article
Chemistry, Applied
Haiping Yang, Shuaishuai Lei, Kun Xu, Yang Fang, Xu Chen, Yingquan Chen, Xianhua Wang, Hanping Chen
Summary: A new method for the efficient preparation of levoglucosenone (LGO) using sulfonated carbon catalyst was proposed in this study. The results showed that the highest selectivity of LGO was achieved at 400 degrees C and a mass ratio of 1:1 for glucose/sulfonated carbon catalyst. Density functional theory calculations demonstrated that sulfonated carbon catalyst facilitated the formation of LGO by altering the reaction pathway.
FUEL PROCESSING TECHNOLOGY
(2022)
Article
Materials Science, Paper & Wood
Feixiang Xu, Jiangchen Luo, Liqun Jiang, Zengli Zhao
Summary: This study improved the production of levoglucosan and levoglucosenone from acid-impregnated cellulose through fast pyrolysis. The impregnation of acid reduced the activation energy and reaction temperature, significantly increasing the yield of levoglucosan. The study demonstrated the potential for industrial production of levoglucosan and levoglucosenone from cellulose at low temperatures.
Article
Engineering, Environmental
Stef Ghysels, Adriana Estrada, Lena Vanderhaeghen, Diederik Rousseau, Ann Dumoulin, Simon Backx, Sven Mangelinckx, Frederik Ronsse
Summary: This pioneering work explores the thermocatalytic conversion of tagua seeds from the palm Phytelephas aequatorialis into key chemical building blocks. The results demonstrate the potential of using mannan-rich feedstock for biorefining and can be applied to other mannan-rich agricultural residues.
CHEMICAL ENGINEERING JOURNAL
(2023)
Article
Chemistry, Physical
Tatsuya Kuremoto, Ren Sadatsune, Tomohiro Yasukawa, Shu Kobayashi
Summary: A novel core/shell structure support was designed to enhance the accessibility of reaction sites, showing higher catalytic activity in asymmetric 1,4-addition reactions. This design strategy may offer a general approach for obtaining other heterogeneous catalysts with high activities.
Article
Materials Science, Paper & Wood
Le Qian, Feixiang Xu, Shijun Liu, Gaojin Lv, Liqun Jiang, Tongchao Su, Yitong Wang, Zengli Zhao
Summary: In this study, a magnetic solid acid Fe3O4/C-SO3H600 was synthesized and proven effective in catalyzing the fast pyrolysis of cellulose to yield high amounts of levoglucosenone (LGO). The research also demonstrated that LGO could be produced through further dehydration of levoglucosan.
Article
Polymer Science
Amandine L. Flourat, Mattia Annatelli, Sami Fadlallah, Fabio Arico, Florent Allais
Summary: A new class of furanic alpha,omega-dienes was synthesized using cellulose-derived starting material, and their properties in acyclic diene metathesis polymerization were investigated. The resulting biobased polyethers showed high molecular weights and good thermal stability, with low glass transition temperatures. The use of green solvents and copolymerization experiments were explored to improve the performance of the polyethers.
Article
Polymer Science
Sami Fadlallah, Quentin Carboue, Louis M. M. Mouterde, Aihemaiti Kayishaer, Yasmine Werghi, Aurelien A. M. Peru, Michel Lopez, Florent Allais
Summary: A renewable five-membered lactone containing citronellol was synthesized and a one-pot two-step pathway was developed to produce a mixture of Lactol-citro molecules. The study found that temperature affects the chemical shifts of the hydroxyls and the 5ML:6ML ratio. Polymers with low glass transition temperatures and cross-linked citronellol chains were successfully prepared.
Article
Agricultural Engineering
Guangchuan Tang, Xin Huang, Anbang Xu, Zhongqing Yang, Changlei Qin, Jingyu Ran
Summary: This study conducted liquid-phase continuous conversion of LGA using SO3H functionalized resin to produce LGO as a bio-renewable platform for fine and commodity chemicals. The highest LGO yield of 38.4% was obtained under optimized conditions. Additionally, the use of bio-oil as substrate promoted LGO yield to 55.4%.
INDUSTRIAL CROPS AND PRODUCTS
(2022)
Article
Chemistry, Organic
Bulat T. Sharipov, Anna N. Davidova, Farid A. Valeev
Summary: Chiral 2-trichloromethyloxazolines were synthesized from levoglucosenone and annulated to a carbohydrate fragment. The compounds were converted to 4-substituted 3-amino-1,6-anhydro-3-deoxy-beta-D-marmopyranoses by acid hydrolysis. Intramolecular amination of allyl trichloroacetimidates was used to construct the oxazoline ring. It was found that trichloroacetimidates with an epoxide ring undergo recyclization to form the oxazoline ring spontaneously.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS
(2022)
Article
Chemistry, Physical
R. L. Safiullin, A. N. Teregulova, A. R. Yarullin, M. Yu Ovchinnikov, S. L. Khursan
Summary: Flash photolysis of aromatic azides leads to the formation of aryl nitroso oxides, which then transform into unsaturated nitrile oxides via aromatic ring opening. The electronic spectra and decay kinetics of the nitroso oxides were investigated, revealing significant differences in the rate constants between cis and trans isomers. The decay process was described by a system of three elementary reactions, and the activation energy barriers were determined using DFT calculations.
KINETICS AND CATALYSIS
(2022)
Article
Chemistry, Organic
B. T. Sharipov, A. N. Davydova, F. A. Valeev
Summary: 3,9-dialkyl-substituted 1,8-cineole derivatives were synthesized through Diels-Alder reactions. The methylated adducts of levoglucosenone with isoprene and butadiene underwent different intramolecular oxacyclization reactions.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Letter
Chemistry, Organic
Nadezhda M. Andriyashina, Stanislav A. Grabovskii, Rustam L. Safiullin
Summary: This study aimed to investigate the thermal stability of 1,1-dihydroperoxycyclohexane in different solvents. The rate constants and activation parameters were measured to determine the reaction rate and the peroxide's monomolecular decomposition rate in the presence of 2-naphthol. The use of DHPC as a radical initiator requires considering its reactions with solvents and/or monomers, as well as its monomolecular decomposition with the formation of free radicals.
LETTERS IN ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Liliya Kh. Faizullina, Yuliya A. Khalilova, Liliya Sh. Karamysheva, Shamil M. Salikhov, Farid A. Valeev
Summary: This study investigated the utilization of Cyrene for the synthesis of trichothecene sesquiterpenoids modified in the central moiety. The reactions and products under different conditions were explored.
MENDELEEV COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Liliya Kh. Faizullina, Artur R. Tagirov, Shamil M. Salikhov, Farid A. Valeev
Summary: Diels-Alder adducts of levoglucosenone with isoprene, butadiene and piperylene can smoothly react with acetaldehyde or benzaldehyde in the presence of AlCl3, resulting in the formation of products of the ene reaction, with the hydroxy group of the primary intermediates participating in the formation of semiketal moiety. The yields of the reaction products are influenced by both the Lewis acid used (AlCl3, BF3.Et2O, ZnBr2, SnCl(4) or EtAlCl2) and the nature of the substrate.
MENDELEEV COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Stanislav A. Grabovskii, Nadezhda M. Andrijashina, Alexandr N. Lobov, Arkadiy V. Antipin, Rustam L. Safiullin
Summary: A facile and efficient method for the oxidation of sulfides to sulfoxides without using any catalysts is reported. The method achieved high yields (> 95%) of sulfoxides under mild conditions. The low cost and ready accessibility of gem-dihydroperoxides make them attractive oxidants for chemical synthesis.
Article
Chemistry, Organic
Liliya Kh. Faizullina, Liliya Sh. Karamysheva, Yuliya A. Khalilova, Shamil M. Salikhov, Farid A. Valeev
Summary: The influence of hydroxy, methyl, and benzyloxy groups in corresponding phenol derivatives on the Michael addition to levoglucosenone in the presence of AlCl3 or FeCl3 was investigated. The reaction between phenols containing hydroxyl and methyl groups in the ortho position with levoglucosenone results in spontaneous ketalization of the carbohydrate keto group. The obtained compounds show promise for studying their structure-activity relationship.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS
(2023)
Article
Polymer Science
Lyaysan R. Latypova, Gulsum S. Usmanova, Liliya Ya. Vasilova, Anastasia N. Andriianova, Samil M. Salikhov, Vladimir V. Zorin, Akhat G. Mustafin
Summary: Polyaniline derivatives containing alkyl and alkenyl fragments were synthesized and characterized. The chemical structures of the polymers were analyzed using NMR, UV-Vis, and FT-IR. SEM images showed different shapes and surface morphology of the polymers. The N-alkenyl PANIs exhibited higher stability and better antibacterial activities against both gram-positive and gram-negative bacteria, making them potential candidates for biomedical applications.
JOURNAL OF POLYMER RESEARCH
(2023)
Article
Chemistry, Multidisciplinary
Lyaysan R. Latypova, Gulsum S. Usmanova, Shamil M. Salikhov, Akhat G. Mustafin
Summary: This study investigates the application of dimethyl sulfoxide and thionyl chloride in organic reactions and explores the effect of carbon chain structure on the types of products formed. The findings provide valuable guidance for organic synthesis.
MONATSHEFTE FUR CHEMIE
(2023)
Article
Materials Science, Multidisciplinary
Gulsum S. Usmanova, Lyaysan R. Latypova, Anastasiia N. Andriianova, Shamil M. Salikhov, Akhat G. Mustafin
Summary: Polymers containing fragments of aniline and indole were synthesized by chemically modifying copolymers of ClPA with Ani of different composition. Their structures and compositions were determined using IR, NMR, UV-spectroscopy, and elemental analysis methods. Morphology, electrochemical characteristics, photoluminescence, thermal stability, and photoconductive properties were evaluated. The modified polymers showed improved thermal stability and the structural changes were observed by electron microscopy. The increase in the photoconductivity of polymer films with a larger number of indole-containing units indicates their potential use in modern electronics.
MATERIALS TODAY COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Lyaysan R. Latypova, Gulsum S. Usmanova, Shamil M. Salikhov, Akhat G. Mustafin
Summary: Dimethyl sulfoxide (DMSO) is a commonly used organic solvent in many organic reactions, and it has been found that the DMSO/SOCl2 system is efficient for the intramolecular cyclization of 2-alkenylanilines. The interaction between N-tosyl derivatives and thionyl chloride in the DMSO/SOCl2 system was studied, and the structure of the obtained products was found to depend on the structure of the alkenyl fragment and the reaction conditions. The new compounds were confirmed by IR, heteronuclear NMR spectroscopy, and high resolution mass spectrometry.
MONATSHEFTE FUR CHEMIE
(2023)
Article
Chemistry, Multidisciplinary
Lilia Kh Faizullina, Artur R. Tagirov, Shamil M. Salikhov, Farid A. Valeev
Summary: This study investigates the reactions of acetaldehyde with low-valence Diels-Alder adducts and reveals the mechanism and product formation. The results demonstrate that acetaldehyde adds to the acetal center and opens the anhydro bridge to form products.
MENDELEEV COMMUNICATIONS
(2022)
