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1
Content available Preparation of conjugated nitroalkenes: short review
Zawadzińska Karolina, Gaurav Gajendra Kumar, Jasiński Radomir
Scientiae Radices
|
2022
|
Vol. 1, Iss. 1
69--83
EN
Key protocols of the preparation of conjugated nitroalkenes were reviewed and critically discussed. It was established, that optimal strategy for the obtaining of target compounds are small molecules extrusion processes from saturated nitro-compounds. Among them, the most universal methodologies based on carboxylic acids elimination have been discussed, which provide for smooth applications.
2
Content available Donorowo-akceptorowe struktury oligopirolowe : projektowanie, synteza i właściwości
Stępień Marcin
Wiadomości Chemiczne
|
2021
|
[Z] 75, 5-6
593--602
EN
The review summarizes one decade of research carried out in the Stępień Laboratory at the University of Wrocław. We focus on the group’s contributions to pyrrole chemistry, notably the development of donor-acceptor pyrrole hybrids and their use as building blocks in the synthesis of porphyrins, small-molecule dyes, and nanographene analogues.
3
Content available remote Ciecze jonowe w metatezie olefin : wyzwania i bariery
Barteczko Natalia, Grymel Mirosława, Chrobok Anna
Przemysł Chemiczny
|
2020
|
T. 99, nr 6
927--933
PL
Metateza olefin stanowi jedno z najskuteczniejszych narzędzi syntezy organicznej w ostatnich latach. Ciecze jonowe (IL) ze względu na ciekawe właściwości, takie jak mała prężność par, możliwość projektowania oraz duża zdolność rozpuszczania szerokiej gamy związków organicznych, nieorganicznych i metaloorganicznych, stosowane są w reakcjach metatezy jako alternatywne rozpuszczalniki wobec różnych układów katalitycznych. Przedstawiono przykłady zastosowania IL w metatezie olefin, a także związane z tym wyzwania i bariery.
EN
A review, with 71 refs., of ionic liqs. used in olefin metathesis as alternative solvents.
4
Content available remote Otrzymywanie i zastosowanie alkoholu 2-metyloallilowego w przemysłowej syntezie organicznej
Żółtański Antoni, Siwak Tomasz
Przemysł Chemiczny
|
2019
|
T. 98, nr 9
1479--1484
PL
Alkohol metyloallilowy, po wdrożeniu w skali technicznej ekonomicznych metod jego otrzymywania, stał się dostępnym surowcem dla przemysłowej syntezy organicznej. Przedstawiono przegląd aktualnej literatury dotyczącej metod produkcji tego związku i kierunków jego dalszych zastosowań, gdzie dominująca pod względem skali jest synteza polikarboksylanowych superplastyfikatorów dla mieszanek betonowych.
EN
A review, with 71 refs., of phys.-chem. properties, synthesis methods and applications mainly as polycarboxylate superplasticizers for concrete as well as an in prodn. of drugs, pesticides and fragrances.
5
Content available Anion alkoksyallenowy w syntezie związków naturalnych i ich analogów
Busiak B., Utecht G., Jasiński M.
Wiadomości Chemiczne
|
2016
|
[Z] 70, 1-2
3--23
EN
Among diverse systems containing multiple bonds, cumulenes are recognized as the most reactive derivatives towards both nucleophilic and electrophilic agents, and for this reason, they are considered as important class of substrates for organic synthesis. Over the last three decades alkoxyallenes have been demonstrated as highly useful C3-building blocks for the construction of numerous N-, O-, and S-containing heterocycles, including enantiomerically pure compounds. Special attention has been paid to lithiated alkoxyallenes as suitable nucleophiles for the reactions with alkyl halides, strained heterocycles, carbonyl compounds and their derivatives. The presence of the allene unit in the initially formed adducts opens up several possibilities in the preparation of more complex systems. In this review, selected applications of lithiated alkoxyallenes in the synthesis of natural products and their analogues are discussed.
6
Content available remote Kwasowe ciecze jonowe jako katalizatory w przemysłowej syntezie organicznej
Matuszek K., Chrobok A.
Przemysł Chemiczny
|
2016
|
T. 95, nr 6
1215--1220
PL
Dokonano przeglądu literatury dotyczącej zastosowania kwasowych cieczy jonowych jako katalizatorów w syntezie organicznej. Ciecze te mogą posiadać centrum kwasowości Lewisa lub Brønsteda ulokowane w strukturze kationu i/lub anionu. Opisano metody wyznaczania kwasowości cieczy jonowych, przedstawiono ich charakterystykę oraz przykłady zastosowania jako katalizatorów w typowych reakcjach katalizowanych za pomocą kwasów (alkilowanie Friedla i Craftsa, reakcja Dielsa i Aldera oraz estryfikacja).
EN
A review, with 58 refs., of Lewis and Brønsted acidic ionic liqs. as catalyst in Friedel-Crafts alkylation, Diels-Alder reaction and esterification.
7
Content available remote Synteza nowych 2-arylo-3-fenylo-4-nitro-tetrahydro-1,2-oksazoli w 1,3-dialkiloimidazoliowej cieczy jonowej
Dresler E., Jasiński R.
Przemysł Chemiczny
|
2015
|
T. 94, nr 12
2244-2246
PL
1,3-Dipolarne cykloaddycje nitroetenu do (Z)-C-fenylo-N-arylonitronów w chlorku 1-butylo-3-metyloimidazoliowym realizują się w temperaturze pokojowej i prowadzą do mieszanin stereoizomerycznych 3,4-cis i 3,4-trans-2-arylo-3-fenylo-4-nitrotetrahydro-1,2-oksazoli z wydajnościami na poziomie 80–85%. Struktury zsyntezowanych oksazoli zostały potwierdzone danymi analizy elementarnej oraz spektroskopii 1H NMR i IR.
EN
1,3-Dipolar cycloaddn. of CH2=CHNO2 to 3-Me, 4-Br, 3-Br and 4-NO2-substituted (Z)-C-phenyl-N-arylnitrones in 1-butyl-3-methylimidazolium chloride at room temperature gave mixts. of 3,4-cis and 3,4-trans-2-aryl-3-phenyl-4-nitrotetrahydro-1,2-oxazoles in yields 80–85%. The structure of the oxazoles was confirmed by elementary anal. as well as 1HNMR and IR spectroscopies.
8
Content available remote Wykorzystanie promieniowania mikrofalowego w syntezie organicznej
Markowski J., Oleksik J.
Przemysł Chemiczny
|
2014
|
T. 93, nr 6
934-937
PL
Przedstawiono przegląd wybranych zastosowań promieniowania mikrofalowego w syntezie organicznej.
EN
A review, with 51 refs., of chem. reactions carried out in microwave field.
9
Content available remote Otrzymywanie i zastosowanie alkoholu allilowego w przemysłowej syntezie organicznej
Żółtański A., Tic W. J.
Przemysł Chemiczny
|
2014
|
T. 93, nr 11
1937-1941
PL
Alkohol allilowy, po opracowaniu i wdrożeniu w skali technicznej tanich metod jego otrzymywania, stał się atrakcyjnym surowcem dla przemysłowej syntezy organicznej. Przedstawiono obecnie stosowane metody produkcji tego związku i kierunki jego dalszych zastosowań, gdzie dominująca pod względem skali jest synteza 1,4-butanodiolu.
EN
A review, with 91 refs., of methods for prodn. of CH₂=CHCH₂OH and its use for manufg. polyester resins, allyl phthalates, copolymers with styrene, oxyethylates and butanediol-1,4.
10
Content available Bezpośrednia synteza azydków i tioli organicznych pochodnych glikolu etylenowego w zmodyfikowanej reakcji Appela
Stefaniak M., Jasiński M., Urbaniak K., Romański J., Seliger P., Gutowska N
Chemik
|
2014
|
Vol. 68, nr 7
592--599
PL
Klasyczną metodę konwersji alkoholi pierwszorzędowych w odpowiednie halogenki alkilowe z użyciem trifenylofosfiny oraz tetrahalogenometanu, tzw. reakcję Appela, zaadoptowano do bezpośredniej syntezy terminalnych tioli i azydków organicznych pochodnych glikolu etylenowego oraz jego siarkowego analogu. W kluczowym etapie opisanej procedury one-pot, otrzymane in situ, w reakcji z N-bromosukcynimidem (NBS), odpowiednie dibromopochodne zostały przekształcone w związki docelowe w reakcji z nukleofilem siarkowym lub azotowym. Wybrane diazydki wykorzystano w syntezie nowych układów makrocyklicznych, które przetestowano pod kątem ich właściwości kompleksotwórczych.
EN
Classical method of conversion of primary alcohols into corresponding alkyl halides by usage of triphenylphosphine and tetrahalogenated methane, so-called Appel reaction, was adopted for the direct synthesis of terminal organic thiols and azides derived from ethylene glycol and its sulfurated analogue. In key step of the presented ‘one-pot’ protocol, corresponding dibromides, generated in situ via reaction with N-bromosuccinimide (NBS), were converted into desired products by treatment with appropriate sulfur or nitrogen nucleophile. A series of diazides and dithiols derived from (poly)ethylene glycols and their sulfur analogues were obtained. Selected diazides were utilized for the construction of novel macrocyclic systems, that were tested incontext of their complexing properties.
11
Content available Kwas winowy i jego pochodne we współczesnej chemii organicznej
Grajewski J.
Wiadomości Chemiczne
|
2013
|
[Z] 67, 5-6
495--519
EN
The tartaric acid and its salts have been present in chemistry for almost 350 years, since Pierre Seignette isolated Rochelle salt in 1675. Since that time tartaric acid and its derivatives have been often used in chemistry due to their accessibility, enantiopurity, relatively low cost and presence of different functional groups which easily allow to modify the molecule. Many tartaric acid derivatives serve as catalysts in important stereoselective transformations such as Sharpless asymmetric epoxidation or asymmetric Rousch aryloboronation. In many others reactions tartaric acid have been employed as a chiral building block for natural products synthesis, highly functionalized molecules or ligand design such as well known TADDOL or its analogues. Its polar functional groups allow to form crystals with amines and aminoalcohols what is widely used for their enantiopurification and resolution. The relatively new subdiscipline is the use of tartaric acid in chiral recognition and chiral discrimination in nanochemistry and enantioselective chromatography. The other, recent applications of tartaric acid include functionalization of metal layers, antibacterial and antifungal activity among many others. The significance of tartaric acid is evident – since 2000, words “tartaric acid” or “tartrates” can be found in databases over four thousand times. Taking that into account this short review is concentrated on selected applications of tartaric acid and its derivatives in organic chemistry in recent several years.
12
Content available Ditlenek węgla w syntezie organicznej
Burczyk B.
Wiadomości Chemiczne
|
2013
|
[Z] 67, 1-2
1--53
EN
Carbon dioxide is an abundant, cheap, almost nontoxic, thermodynamically stable, inert electrophile. Exploitation of CO 2 as a chemical feedstock, although will almost certainly not reduce its atmospheric concentration significantly, aims to generate high-value products and more-efficient processes. In recent years efficient transition-metal complexes have been used to perform homogeneously catalyzed transformations of CO 2 . This paper presents an overview of available catalytic routes for the synthesis of carboxylic acids, lactones, urea and carbamates, linear and cyclic carbonates as well as polycarbonates. Reduction processes of CO 2 are shortly men - tioned as well. C arboxylic acids have been synthesized via : (i) carboxylation of organolithium, organomagnesium (Scheme 2 [35]), organoboron (Scheme 3 [40 -42]), organozinc (Scheme 4 [43, 44]) and organotin (Scheme 5 [45, 46]) compounds; (ii) oxidative cycloaddition of CO 2 to olefins and alkynes (Scheme 6 -10 [47 -50, 57]) catalyzed by Ni(0)-complexes; (iii) transition-metal catalyzed reductive hydrocarboxylation of unsaturated compounds (Scheme 11, 12 [64 -67]); (iv) carboxylation of C-H bond (Scheme 13 [69 -71]). Telomerization of dienes, for instance 1,3-butadiene, and CO 2 in the presence of Ni(II) and Pd(II) complexes leads to lactones and esters of carboxylic acids (Scheme 14, 15 [73 -79]). Nucleophilic ammonia, primary and secondary amines react with CO 2 to give, respectively, urea and carbamic acid esters - carbamates and isocyanates (Scheme 16 -18 [94, 95]), thus eliminating the use of phosgene in their synthesis. CO 2 reacts with alcohols, diols and epoxides in the presence of transition-metal complexes (Fig. 2) and the reaction products are: linear carbonates (Scheme 20, 21 [110 -118]), cyclic carbonates (Scheme 22 -24 [153 -170]) and polycarbonates (Scheme 25, 26, Fig. 3, Tab. 1 [179 -186]). Finally, hydrogenation of CO 2 , leading to the formation of CO, HCOOH, CH 3 OH, CH 4 , C 2 H 6 and C 2 H 4 (Scheme 27), as well as electrochemical and photochemical reductions in the pre - sence of homogeneous and heterogeneous catalysts have been shortly reviewed.
13
Content available remote Kompleks mocznikowo-wodoronadtlenkowy jako efektywny i ekologiczny czynnik utleniający w syntezie organicznej
Podraza A., Pielichowski J.
Przemysł Chemiczny
|
2013
|
T. 92, nr 2
158-164
14
Content available Mikrofale w syntezie organicznej: historia i perspektywy
Lipińska T. M
LAB Laboratoria, Aparatura, Badania
|
2013
|
R. 18, nr 4
6--10
15
Content available Biokatalityczne metody otrzymywania nieracemicznych alkoholi aryloallilowych
Szymkuć S., Ostaszewski R.
Wiadomości Chemiczne
|
2012
|
[Z] 66, 1-2
93-118
EN
Different methods for preparing nonracemic arylallylic alcohols are presented in this work. A key feature was an application the biocatalyst as a mean to obtain final products. These compounds play an important role in pharmaceutical industry, because they are substrates in the synthesis of various important therapeutics [1–3]. Methods presented in this work are divided into five main groups: 1. enantioselective hydroxylation, 2. microbiological deracemization, 3. enzymatic kinetic resolution, 4. enzymatic dynamic kinetic resolution, 5. enantioselective reduction. First two methods use only microorganisms like bacteria [4, 5, 10], fungi [6–8] or yeasts [11] as biocatalysts. Owing to the metabolic processes in the cells it was possible to obtain nonracemic arylallylic alcohol (results for method 2 are presented in Table 1). Unfortunately, the data were insufficient to create direct correlation between values of enantiomeric excess and types of applied microorganisms. Methods 3 and 4 used only isolated enzymes as biocatalysts. They belong to two classes: hydrolases and oxidoreductases. Oxidoreductases were used in the enzymatic kinetic resolution based on the enantioselective oxidation [28] of one enantiomer of the racemic arylallylic alcohol. Nevertheless, hydrolases [12–27], mainly lipases, isolated from microorganisms are enzymes of common use in enzymatic kinetic resolution. Owing to this method it was possible to obtain final products with excellent enantioselectivity (results are presented in Tables 2 and 3). Because kinetic resolution and dynamic kinetic resolution are related processes, in most cases similar enzymes are used. The choice of lipases as biocatalysts for method 4 was caused by the fact that they are able to catalyze enantioselective transesterification of arylallylic alcohols or their acetates. Furthermore, racemization is very important factor for efficacy of dynamic kinetic resolution processes. In most cases they are catalyzed by different types of complexes based on palladium [30, 31] and ruthenium [32, 34]. Final products prepared by this method had very high enantiomeric excesses and yields up to 93% (results are presented in Tables 4 and 5). The only method, presented in this work, that allowed to use both enzymes [39–41] and microorganisms [35–38] as biocatalysts, was enantioselective reduction. This method allows to obtain nonracemic arylallylic alcohols with excellent enantiomeric excess and yields up to 85% (results are presented in Table 6). In summary, all methods presented in this work show the advantages of biocatalysis as an alternative route to traditional chemical method
16
Content available Zastosowania wybranych enzymów z tkanek zwierzęcych w syntezie organicznej i biokatalizie. Część II. Oksydoreduktazy, transferazy, liazy, izomerazy
Hibner H., Ostaszewski R.
Wiadomości Chemiczne
|
2011
|
[Z] 65, 7-8
585-607
EN
This work shows systematically known types of animal enzymes and their applications in synthesis of pharmaceuticals and nonracemic organic compounds. It lays out similarities in procedures of isolation and purification of particular enzymes. Such procedures usually are so simple that they can be used in every industrial or research laboratory. Most animal enzymes are well-investigated and their structures and substrate specificity are known. They are used as biocatalysts in many chemical processes. Others were used in one or a few reactions but their natural substrates and biochemical properties are described. Trials of predicting potential applications of such enzymes and other substrates for them were performed. Typical applications of: – Oxidoreductases: horse liver alcohol dehydrogenase [3–13], lactate dehydrogenase [16–18], glutamate dehydrogenase [19, 20], carbonyl reductase [24], catalase [27]; – Transferases: transaldolase [29], galactosyltransferase [30], UDP-glucuronosyltransferase [31], fucosyltransferase [34], farnesyl diphosphate synthase [35]; – Lyases: DOPA decarboxylase [38, 39], aldolase [42]; – Isomerases: N-acyl-D-glucosamine 2-epimerase [44] were described. Also examples of or recombined [24, 39, 44] enzymes are given in the text. These modifications enhance catalytic properties or reduce costs of using enzymes. In practical applications a biocatalytic effect of enzymes from animal sources is often compared with microbial ones. This text is focused on processes where animal enzymes gave much better results (yield and enantioselectivity) than microorganisms. They are also proper, unlike whole microorganisms, to investigate and computer analysis of mechanism of the reaction. Enzymes isolated from animal tissues usually have well-defined structure of active site which is a key to predict mechanisms. A quantitative analysis of applications of these enzymes was performed. Among animal enzymes hydrolases and oxidoreductases have found the most applications in synthesis. Transferases are also often used. Other classes of enzymes seldom act as biocatalysts. It is general tendency, true also in relation to microbial and plant enzymes.
17
Content available Zastosowania enzymów z tkanek zwierzęcych w syntezie organicznej i biokatalizie. Część I. Hydrolazy
Hibner H., Ostaszewski R.
Wiadomości Chemiczne
|
2011
|
[Z] 65, 7-8
557-583
EN
This work presents systematically enzymes which can be obtained form animal tissue and their applications in synthesis of pharmaceuticals and nonracemic organic compounds. It lays out similarities in procedures of isolation and purification of particular enzymes. Such procedures usually are so simple that they can be used in every industrial or research laboratory. Most animal enzymes are well-investigated and their structures and substrate specificity are known. They are used as biocatalysts in many chemical processes. Others were used in one or a few reactions but their natural substrates and biochemical properties are described. Trials of predicting potential applications of such enzymes and other substrates for them were done. In this part typical applications of hydrolases: lipases (porcine pancreatic lipase [8–17], lamb pregastric lipase [22]), esterases (porcine, horse liver esterase, liver acetone powders [34–43, 46]), L-aminoacylase [48, 49], pepsin [56], trypsin [58, 59], imidase [52, 53], aldohexose hydrolases [60, 62-64], nucleotide pyrophosphatase [65]; were described. Also examples of immobilized [10, 32] or recombined [49] enzymes are given in the text. These modifications enhance catalytic properties or reduce costs of using enzymes. In practical applications a biocatalytic effect of enzymes from animal sources is often compared with microbial ones. This text is focused on processes where animal enzymes gave much better results (yield and enantioselectivity) than microorganisms. They are also proper, unlike whole microorganisms, to investigate and computer analysis of mechanism of the reaction. Enzymes isolated from animal tissues usually have well-defined structure of active site which is a key to predict mechanisms.
18
Content available remote Komputerowe projektowanie wieloetapowych syntez organicznych : stan aktualny i kierunki rozwoju
Nowak G., Fic G.
Przemysł Chemiczny
|
2011
|
T. 90, nr 1
78-83
19
Content available remote Biotransformacje z udziałem drożdży
Białecka-Florjańczyk E., Krzyczkowska J., Stolarzewicz I.
Przemysł Chemiczny
|
2011
|
T. 90, nr 5
691-695
20
Content available remote Desililujące sprzęganie winylosilanów i etynylosilanów w sekwencjach reakcji w syntezie organicznej
Prukała W.
Wiadomości Chemiczne
|
2008
|
[Z] 62, 9-10
779-826
EN
An efficient formation of carbon-carbon bonds belongs to one of the most important transformations in synthetic chemistry. The reaction is predominantly catalyzed by the late transition metals [1, 2]. Traditional methods that have been employed, to accomplish this transformation include Stille and Suzuki reactions. However, due to a number of drawbacks inherent to the substrates used in these reactions, organosilicon reagents have emerged as competitive alternatives (the facility of preparation and purification of silanes, their high stability, and low-molecular weight). Because of the low polarizability of the C-Si bond, the silicon function must undergo nucleophilic activation to induce migration of a transferable group onto the organopalladium species (transmetallation) [3-8]. The family of palladium-based catalysts, used in the desilylative coupling reaction (DC), tolerates the presence of the majority of functional groups. The paper gives a review of literature focused on the application of desilylative coupling in sequential reactions published till the end of 2007. The activity of different catalytic systems based on palladium compounds in desilylative coupling reactions has been characterized. The influence of some substituents and activators on the reaction as well as their mechanisms has been presented [36, 41, 94-104]. It is remarkable, that the two entirely different mechanisms can be operative for both fluoride and fluoride-free silanolate couplings [104-110], and that both are highly efficient room temperature reactions. Alkenylsilanes, used in sequential reactions, can be efficiently prepared by several stereo- and regioselective methodologies involving classical stoichiometric routes from organometallic reagents and, more recently, transition-metal-catalyzed transformations of alkynes and silylalkynes (via the hydrosilylation, Sonogashira reaction), alkenes (the dehydrogenative silylation [10, 12, 13], cross-metathesis [9-11], Heck reaction), and other silicon derivatives. Moreover, the paper provides a characterization of the desilylative coupling reaction (DC) conditions. Several independent sequential reactions (one-pot, tandem reaction), e.g. RCM/DC, Stille/DC, Heck/DC, Sonogashira/DC, cross-metathesis/DC, silylative coupling/DC etc., and their applications to the synthesis of biologically active compounds have been presented. The paper is completed with a list of the most important, in the author's opinion, monographs and review works on the application of the desilylative coupling catalysed by palladium compounds in organic synthesis.
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