Indene dimerization products
Proizvodi dimerizacije indena
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The reaction of 1H-indene (indene) in the presence of Friedel-Crafts acids was studied. As expected [M. Spiteller, J. Jovanović, Fuel 78(1999)1263] there were dimers and trimers in the product mixture together with higher oligomers. Among products with double molecular weight relative to the molecular weight of indene, the structure of four compounds was determined: 6-(2’,3’-dihydro-1’H-inden-1’-yl)-1H-indene 2-(2’,3’-dihydro-1’H-inden-1’-yl)-1H-indene 1-(2’,3’-dihydro-1’H-inden-2’-yl)-1H-indene and 2,3,1’,3’-tetrahydro-[1,2’]biindenylidene. It was shown that the first one represents an indene alkylation product and that the others were obtained by bonding of the indan-1-ylium ion and indene at the position 2, followed by acid catalyzed 1,2-hydride rearrangement in the case of the third and fourth one. Considering the indene dimerization products as components of pyrolysis oils and as interesting compounds to be used as model substances for NMR, MS and X-ray analysis, the reaction, sep...aration and isolation parameters were optimized in this study.
Ispitivana je reakcija 1H-indena u prisustvu Fridel-Kraftsovih kiselina. Kao što je i očekivano,1 smeša proizvoda je sadržala dimere, trimere i više oligomere. Među proizvodima sa dvostrukom molskom masom, u odnosu na molsku masu indena, određena je struktura četiri jedinjenja 6-(2’,3’-dihidro-1’H-inden-1’-il)-1H-indena 2-(2’,3’-dihidro-1’H-inden-1’-il)-1H-indena 1-(2’,3’-dihidro-1’H-inden-2’-il)-1H-indena i 2,3,1’,3’-tetrahidro-[1,2’]biindenilidena. Pokazano je da je prvo jedinjenje proizvod alkilacije indena, a da su preostala tri dobivena povezivanjem indena u položaju 2 sa indan-1-ilijum jonom, pri čemu je u slučaju trećeg i četvrtog jedinjenja došlo i do 1,2-hidridnog premeštanja. Uzimajući u obzir da su proizvodi dimerizacije indena komponente pirolitičkih ulja i interesantna jedinjenja kao modeli za NMR i MS analize i analize pomoću X-zraka, u ovom radu je optimizirano njihovo dobijanje, razdvajanje i izolovanje.
Кључне речи:
dimers of indene / structure elucidation / NMR spectroscopy / MS spectrometry / HPLC chromatographyИзвор:
Journal of the Serbian Chemical Society, 2002, 67, 6, 393-406Издавач:
- Serbian Chemical Society, Belgrade
Институција/група
Tehnološko-metalurški fakultetTY - JOUR AU - Jovanović, Jovan AU - Spiteller, Michael AU - Elling, Wilhelm PY - 2002 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/449 AB - The reaction of 1H-indene (indene) in the presence of Friedel-Crafts acids was studied. As expected [M. Spiteller, J. Jovanović, Fuel 78(1999)1263] there were dimers and trimers in the product mixture together with higher oligomers. Among products with double molecular weight relative to the molecular weight of indene, the structure of four compounds was determined: 6-(2’,3’-dihydro-1’H-inden-1’-yl)-1H-indene 2-(2’,3’-dihydro-1’H-inden-1’-yl)-1H-indene 1-(2’,3’-dihydro-1’H-inden-2’-yl)-1H-indene and 2,3,1’,3’-tetrahydro-[1,2’]biindenylidene. It was shown that the first one represents an indene alkylation product and that the others were obtained by bonding of the indan-1-ylium ion and indene at the position 2, followed by acid catalyzed 1,2-hydride rearrangement in the case of the third and fourth one. Considering the indene dimerization products as components of pyrolysis oils and as interesting compounds to be used as model substances for NMR, MS and X-ray analysis, the reaction, separation and isolation parameters were optimized in this study. AB - Ispitivana je reakcija 1H-indena u prisustvu Fridel-Kraftsovih kiselina. Kao što je i očekivano,1 smeša proizvoda je sadržala dimere, trimere i više oligomere. Među proizvodima sa dvostrukom molskom masom, u odnosu na molsku masu indena, određena je struktura četiri jedinjenja 6-(2’,3’-dihidro-1’H-inden-1’-il)-1H-indena 2-(2’,3’-dihidro-1’H-inden-1’-il)-1H-indena 1-(2’,3’-dihidro-1’H-inden-2’-il)-1H-indena i 2,3,1’,3’-tetrahidro-[1,2’]biindenilidena. Pokazano je da je prvo jedinjenje proizvod alkilacije indena, a da su preostala tri dobivena povezivanjem indena u položaju 2 sa indan-1-ilijum jonom, pri čemu je u slučaju trećeg i četvrtog jedinjenja došlo i do 1,2-hidridnog premeštanja. Uzimajući u obzir da su proizvodi dimerizacije indena komponente pirolitičkih ulja i interesantna jedinjenja kao modeli za NMR i MS analize i analize pomoću X-zraka, u ovom radu je optimizirano njihovo dobijanje, razdvajanje i izolovanje. PB - Serbian Chemical Society, Belgrade T2 - Journal of the Serbian Chemical Society T1 - Indene dimerization products T1 - Proizvodi dimerizacije indena EP - 406 IS - 6 SP - 393 VL - 67 UR - https://hdl.handle.net/21.15107/rcub_technorep_449 ER -
@article{ author = "Jovanović, Jovan and Spiteller, Michael and Elling, Wilhelm", year = "2002", abstract = "The reaction of 1H-indene (indene) in the presence of Friedel-Crafts acids was studied. As expected [M. Spiteller, J. Jovanović, Fuel 78(1999)1263] there were dimers and trimers in the product mixture together with higher oligomers. Among products with double molecular weight relative to the molecular weight of indene, the structure of four compounds was determined: 6-(2’,3’-dihydro-1’H-inden-1’-yl)-1H-indene 2-(2’,3’-dihydro-1’H-inden-1’-yl)-1H-indene 1-(2’,3’-dihydro-1’H-inden-2’-yl)-1H-indene and 2,3,1’,3’-tetrahydro-[1,2’]biindenylidene. It was shown that the first one represents an indene alkylation product and that the others were obtained by bonding of the indan-1-ylium ion and indene at the position 2, followed by acid catalyzed 1,2-hydride rearrangement in the case of the third and fourth one. Considering the indene dimerization products as components of pyrolysis oils and as interesting compounds to be used as model substances for NMR, MS and X-ray analysis, the reaction, separation and isolation parameters were optimized in this study., Ispitivana je reakcija 1H-indena u prisustvu Fridel-Kraftsovih kiselina. Kao što je i očekivano,1 smeša proizvoda je sadržala dimere, trimere i više oligomere. Među proizvodima sa dvostrukom molskom masom, u odnosu na molsku masu indena, određena je struktura četiri jedinjenja 6-(2’,3’-dihidro-1’H-inden-1’-il)-1H-indena 2-(2’,3’-dihidro-1’H-inden-1’-il)-1H-indena 1-(2’,3’-dihidro-1’H-inden-2’-il)-1H-indena i 2,3,1’,3’-tetrahidro-[1,2’]biindenilidena. Pokazano je da je prvo jedinjenje proizvod alkilacije indena, a da su preostala tri dobivena povezivanjem indena u položaju 2 sa indan-1-ilijum jonom, pri čemu je u slučaju trećeg i četvrtog jedinjenja došlo i do 1,2-hidridnog premeštanja. Uzimajući u obzir da su proizvodi dimerizacije indena komponente pirolitičkih ulja i interesantna jedinjenja kao modeli za NMR i MS analize i analize pomoću X-zraka, u ovom radu je optimizirano njihovo dobijanje, razdvajanje i izolovanje.", publisher = "Serbian Chemical Society, Belgrade", journal = "Journal of the Serbian Chemical Society", title = "Indene dimerization products, Proizvodi dimerizacije indena", pages = "406-393", number = "6", volume = "67", url = "https://hdl.handle.net/21.15107/rcub_technorep_449" }
Jovanović, J., Spiteller, M.,& Elling, W.. (2002). Indene dimerization products. in Journal of the Serbian Chemical Society Serbian Chemical Society, Belgrade., 67(6), 393-406. https://hdl.handle.net/21.15107/rcub_technorep_449
Jovanović J, Spiteller M, Elling W. Indene dimerization products. in Journal of the Serbian Chemical Society. 2002;67(6):393-406. https://hdl.handle.net/21.15107/rcub_technorep_449 .
Jovanović, Jovan, Spiteller, Michael, Elling, Wilhelm, "Indene dimerization products" in Journal of the Serbian Chemical Society, 67, no. 6 (2002):393-406, https://hdl.handle.net/21.15107/rcub_technorep_449 .