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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

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2014

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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.

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Ocena procesu kofermentacji mieszaniny pomiotu kurzego, organicznej biomasy roślinnej i osadów ściekowych

Borowski S., Romański J.

Ekologia i Technika

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2009

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R. 17, nr 4

182-186

PL

Przeprowadzono badania laboratoryjne kofermentacji pomiotu kurzego i odpadów roślinnych z osadami ściekowymi w warunkach statycznych. Mezofilnej fermentacji beztlenowej poddano mieszaniny osadów wstępnego i nadmiernego z Grupowej Oczyszczalni Ścieków w Łodzi z pomiotem pochodzącym z hodowli bezściółkowej kur-niosek w Zgierzu oraz organicznymi odpadami roślinnymi. W toku badań wykazano, iż osad nadmierny oraz jego mieszanina z osadem wstępnym charakteryzują się stosunkowo wysoką podatnością na rozkład beztlenowy i wydzielanie biogazu, jednakże dodatek pomiotu kurzego do tych osadów zwiększa tą podatność. Najkorzystniejsze efekty uzyskano stosując mieszaninę osadów nadmiernego l wstępnego z pomiotem w proporcjach objętośclowych 65 : 25 : 10. Kofermentacja tej mieszaniny prowadziła do uzyskania 0,42 dm3 biogazu z kg suchej masy organicznej doprowadzonej do komory oraz ponad 50 % redukcji masy organicznej. Stwierdzono również, iż biomasa roślinna jest mało podatna na rozkład beztlenowy, gdyż nawet jej niewielki, 10 % dodatek do osadów niekorzystnie wpływał na wytwarzanie biogazu.

EN

A study of the anaerobic co-digestion of sewage sludge with poultry manure and organic biowaste in a laboratory batch conditions was undertaken. The anaerobic mesophilic digestion was applied for the treatment of primary and waste activated sludge from Municipal Wastewater Treatment Plant in Łódź together with manure from non-litter poultry farming in Zgierz and with organic biowaste. It was found that waste activated sludge itself and its mixture with primary sludge had a relatively large potential for biogas production and anaerobic decomposition, however, a 10 % addition of poultry manure significantly increased this yield. The mixture of primary and waste activated sludge with poultry manure in the ratio of 65 : 25 : 10 turned out to be the most optimal in terms of the digestion efficiency. The co-digestion of that mixture lead to yield 0,42 dm3 biogas from l kg of organic solids, and to obtain the organic soils reduction of over 50 %. A poor biodegradability of organic biowaste was also reported since even a 10 % addition of that waste to the sludge inhibited the biogas production during digestion.

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Reactions of ‘Cage’ Dione with Primary Amines; Revision of an Earlier Report

Romański J.

Polish Journal of Chemistry

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2007

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Vol. 81, nr 2

187-191

EN

Reactions of pentacyclo[5.4.0.02,6.03,10.05,9]undecane-8,11-dione (1, ‘cage’ dione) with primary amines (i.e. benzylamine, aniline, methylamine and 2-aminoethanol) leading to the adducts 4a–d in good yields are described. In all cases the transannular cyclization process was observed and oxa-bridged products 4a–d were obtained. Isolated compounds were identified as hemiacetals or their internal salts. The type of the formed product is dependent on basicity of the used amines. Subsequent dehydration of the initially obtained adducts in boiling benzene led to monoimines 3a–d..

4

Synthesis and Structure of Spirocyclic Tetrahydrothiophene Derivatives Bearing a 'Cage' Residue

Romański J., Mlostoń G., Linden A., Heimgartner H.

Polish Journal of Chemistry

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2005

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Vol. 79 / nr 6

973-979

EN

Trapping of the thiocarbonyl S-methanide 4 with tetracyanoethene and N-methylmaleimide led to the [3+2]-cycloadducts 11 and 12, respectively. The structures of these cycloadducts were established by X-ray crystallography. The 1,3-dipole 4 has been generated by thermal decomposition of the corresponding 2,5-dihydro-1,3,4-thiadiazole 2, which was prepared by the 1,3-dipolar cycloaddition of diazomethane with thioketone 1.

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New Functionalized Derivatives of Sulfur- and Oxygen-Containing Hexacyclic Cage Compounds

Romański J., Marchand A.

Polish Journal of Chemistry

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2004

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Vol. 78 / nr 2

223-230

EN

Several new sulfur- and oxygen-bridged hexacyclic cage compounds have been obtained via transannular cyclization of pentacyclo[5.4.0.02,6.03,10.05,9]undecane-8,11-dione (1). Thus, cage-annulated thiapodands 9 and 10 were prepared via reaction of ditosylate 6 with 2-mercaptoethylamine (7) or 2-mercaptoethanol (8), respectively. Other ditosylate 11 was reacted with thiourea to afford the corresponding dimercapto podand 12. An optically active podand (R,R)-14 was prepared in similar fashion by reacting ditosylate 6 with (R)-2-amino-1-butanol (R)-(13). Functionalized 4-thiahexacyclo[ 5.4.1.0.02,6.03,10 .05,9.08,11]dodecanes 17a-band18a-b were prepared via reactions of 1 with 2-chloro- (15) or 2-bromoethanol (16), respectively in the presence of H2S(g) and HCl(g). The corresponding reaction of 1 with 2 equivalents of 8 produced the corresponding bisthioacetal 20, which subsequently was changed into a spiro-cage-annulated dithiacrown ether 22.

6

Stacje odzysku czynników chłodniczych CPS CR

Romański J.

Chłodnictwo i Klimatyzacja

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2004

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nr 8

26-26

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Effect of the Electrode Material on the Electrochemical Reduction of Some 2,5-Dihydro-1,3,4-thiadiazoles

Turowska M., Mlostoń G., Romański J., Raczak J.

Polish Journal of Chemistry

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2003

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Vol. 77 / nr 2

237-250

EN

During cyclic voltammetric studies of the 2,5-dihydro-1,3,4-thiadiazoles (_3-1,3,4- thiadiazolines) (1a-e) onHMDEin 0.1_10-3 mol/dm3 LiClO4 acetonitrile and aqueousacetonitrile or aqueous-ethanol Britton-Robinson's buffer solutions in second polarization cycle, besides peaks equivalent to polarographic waves, an additional new system of peaks was observed. The corresponding analogous system of additional peaks has not been observed during the reduction of these substances on electrodes of other materials, as i.e., platinum, gold or glassy carbon. This study showed that it results from the oxidation and reduction of organo-mercury compounds, formed in reaction of the electrode material (Hg) with an adsorbed product of 2,5-dihydro-1,3,4-thiadiazoles reduction.

8

Reaction of 2,2,4,4-Tetramethyl-3-thioxocyclobutanone with Dimethyl Diazomalonate Catalyzed by Rh2(OAc)4

Mlostoń G., Romański J., Heimgartner H.

Polish Journal of Chemistry

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2002

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Vol. 76 / nr 4

551-555

EN

The reaction of 2,2,4,4-tetramethyl-3-thioxocyclobutanone (1) with dimethyl diazomalonate in the presence of Rh2(OAc)4 in toluene at 50_C yielded a mixture of three products 10, 11, and 12. Thiocarbonyl ylide 8 is believed to be the common intermediate. The formation of 10 is rationalized by the 1,3-dipolar electrocyclization of 8 to give spirocyclic thiirane 9, which spontaneously eliminated sulfur. On the other hand, the 1,5- dipolar electrocyclization of 8 led to 1,3-oxathiole 11, which is converted into lactone 12 by hydrolysis.

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Reactions of Thioesters with Organic Azides-A Novel Accesss to Imidates and Thioimidates

Mlostoń G., Romański J., Heimgartner H.

Polish Journal of Chemistry

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2001

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Vol. 75, nr 7

975-982

EN

The reaction of O-methyl thiocarboxylates 8a, b with organic azides at 110_C yielded the corresponding imidates of type 9, which were easily hydrolyzed to give amides 10. The formation of 9 can be rationalized by a 1,3-dipolar cycloaddition of the azide with the C=S group, followed by the "twofold extrusion" ofN2 and S. The analogous reaction with methyl dithiobenzoate (11) led to thioimidates 13. On heating, the latter were transformed into thioamides 12.

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A novel type of ring closure of amino-substituted thiocarbonyl ylides

Romański J., Mlostoń G., Linden A., Heimgartner H.

Polish Journal of Chemistry

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1999

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vol. 73 nr 3

475-485

EN

The reaction of 4,4-dimethyl-1,3-thiazole-5(4H)-thiones 7a-c with dimethyl 2-diazo-3-(phenyloamino)butanoate (2), prepared from dimethyl fumarate and phenyl azide, in toluene at 800C yielded mixtures of dimethyl 2-(4,5-dihydro-4,4-dimethyl-1,3-thiazol-5-ylidene)-3-(N-phenylamino)butanedioates of type 11 and four diastereoisometric 4,4-dimethyl-9-phenyl-1,6-dithia-3,9-diazaspiro[4,4]non-2-ene-7,8-dicarboxylates of type 12. The formation of the products of type 12 is rationalized by a novel cyclization of intermediate thiocarbonyl ylides 9. The structures of cis-12a, cis-12c, and trans-12c were established by X-ray crystallography.