NMR analysis of (1S, 1aR, 6aR)-2’, 3’, 6, 6a-tetrahydrospiro cycloprop a indene-1(1aH), 1’- 1H indene
NMR analiza (1S,1aR,6aR)-2’,3’,6,6a-tetrahidro-spiro[cikloprop[a]inden-1(1ah),1’-[ 1h]indena]
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The aldol condensation product of 1H-indan-1-one, (2E)-2-(2,3-dihydro-1H-in den-1-ylidene)-2,3-dihydro-1H-inden-1-one, subjected to Huang–Minlon reduction conditions was shown, via 1D and 2D NMR analysis, to be a mixture of (1S,1aR,6aR)-2’,3’,6,6a-tetrahydro-spiro cycloprop a indene-1(1aH),1’ 1H indene and its 1R,1aS,6aS enantiomer and not 2,3,1’,3’-tetrahydro- 1,2’ -biindenylidene as originally expected. The full NMR assignment, the coupling constants in the proton NMR, and the couplings in the HMBC and NOESY of the title compound are summarized in the Table.
Pokazano je pomoću 1D i 2D NMR analize da (2E)-2-(2,3-dihidro-1H-inden-1-iliden)-2, 3-dihidro-1H-inden-1-on, dobiven aldolnom kondenzacijom 1H-indan-1-ona, podvrgnut Huang–Minlonovoj redukciji daje smešu (1S,1aR,6aR)-2’,3’,6 6a-tetrahidro-spiro[cikloprop[a]inden-1(1aH),1’-[1H]indena] i njegovog 1R,1aS,6aS enantiomera, a ne 2,3,1’,3’-tetrahidro-[1,2’]-biindeniliden kako se prvobitno očekivalo. Potpuni NMR raspored, konstante kuplovanja protona i HMBC i NOESY kuplovanje jedinjenja u naslovu dati su zbirno u tabeli.
Ključne reči:
dimer of indene / NMR assignment / JHH / HMBC / NOESYIzvor:
Journal of the Serbian Chemical Society, 2005, 70, 10, 1133-1136Izdavač:
- Serbian Chemical Society, Belgrade
Institucija/grupa
Tehnološko-metalurški fakultetTY - JOUR AU - Spiteller, Peter AU - Jovanović, Jovan AU - Spiteller, Michael PY - 2005 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/795 AB - The aldol condensation product of 1H-indan-1-one, (2E)-2-(2,3-dihydro-1H-in den-1-ylidene)-2,3-dihydro-1H-inden-1-one, subjected to Huang–Minlon reduction conditions was shown, via 1D and 2D NMR analysis, to be a mixture of (1S,1aR,6aR)-2’,3’,6,6a-tetrahydro-spiro cycloprop a indene-1(1aH),1’ 1H indene and its 1R,1aS,6aS enantiomer and not 2,3,1’,3’-tetrahydro- 1,2’ -biindenylidene as originally expected. The full NMR assignment, the coupling constants in the proton NMR, and the couplings in the HMBC and NOESY of the title compound are summarized in the Table. AB - Pokazano je pomoću 1D i 2D NMR analize da (2E)-2-(2,3-dihidro-1H-inden-1-iliden)-2, 3-dihidro-1H-inden-1-on, dobiven aldolnom kondenzacijom 1H-indan-1-ona, podvrgnut Huang–Minlonovoj redukciji daje smešu (1S,1aR,6aR)-2’,3’,6 6a-tetrahidro-spiro[cikloprop[a]inden-1(1aH),1’-[1H]indena] i njegovog 1R,1aS,6aS enantiomera, a ne 2,3,1’,3’-tetrahidro-[1,2’]-biindeniliden kako se prvobitno očekivalo. Potpuni NMR raspored, konstante kuplovanja protona i HMBC i NOESY kuplovanje jedinjenja u naslovu dati su zbirno u tabeli. PB - Serbian Chemical Society, Belgrade T2 - Journal of the Serbian Chemical Society T1 - NMR analysis of (1S, 1aR, 6aR)-2’, 3’, 6, 6a-tetrahydrospiro cycloprop a indene-1(1aH), 1’- 1H indene T1 - NMR analiza (1S,1aR,6aR)-2’,3’,6,6a-tetrahidro-spiro[cikloprop[a]inden-1(1ah),1’-[ 1h]indena] EP - 1136 IS - 10 SP - 1133 VL - 70 UR - https://hdl.handle.net/21.15107/rcub_technorep_795 ER -
@article{ author = "Spiteller, Peter and Jovanović, Jovan and Spiteller, Michael", year = "2005", abstract = "The aldol condensation product of 1H-indan-1-one, (2E)-2-(2,3-dihydro-1H-in den-1-ylidene)-2,3-dihydro-1H-inden-1-one, subjected to Huang–Minlon reduction conditions was shown, via 1D and 2D NMR analysis, to be a mixture of (1S,1aR,6aR)-2’,3’,6,6a-tetrahydro-spiro cycloprop a indene-1(1aH),1’ 1H indene and its 1R,1aS,6aS enantiomer and not 2,3,1’,3’-tetrahydro- 1,2’ -biindenylidene as originally expected. The full NMR assignment, the coupling constants in the proton NMR, and the couplings in the HMBC and NOESY of the title compound are summarized in the Table., Pokazano je pomoću 1D i 2D NMR analize da (2E)-2-(2,3-dihidro-1H-inden-1-iliden)-2, 3-dihidro-1H-inden-1-on, dobiven aldolnom kondenzacijom 1H-indan-1-ona, podvrgnut Huang–Minlonovoj redukciji daje smešu (1S,1aR,6aR)-2’,3’,6 6a-tetrahidro-spiro[cikloprop[a]inden-1(1aH),1’-[1H]indena] i njegovog 1R,1aS,6aS enantiomera, a ne 2,3,1’,3’-tetrahidro-[1,2’]-biindeniliden kako se prvobitno očekivalo. Potpuni NMR raspored, konstante kuplovanja protona i HMBC i NOESY kuplovanje jedinjenja u naslovu dati su zbirno u tabeli.", publisher = "Serbian Chemical Society, Belgrade", journal = "Journal of the Serbian Chemical Society", title = "NMR analysis of (1S, 1aR, 6aR)-2’, 3’, 6, 6a-tetrahydrospiro cycloprop a indene-1(1aH), 1’- 1H indene, NMR analiza (1S,1aR,6aR)-2’,3’,6,6a-tetrahidro-spiro[cikloprop[a]inden-1(1ah),1’-[ 1h]indena]", pages = "1136-1133", number = "10", volume = "70", url = "https://hdl.handle.net/21.15107/rcub_technorep_795" }
Spiteller, P., Jovanović, J.,& Spiteller, M.. (2005). NMR analysis of (1S, 1aR, 6aR)-2’, 3’, 6, 6a-tetrahydrospiro cycloprop a indene-1(1aH), 1’- 1H indene. in Journal of the Serbian Chemical Society Serbian Chemical Society, Belgrade., 70(10), 1133-1136. https://hdl.handle.net/21.15107/rcub_technorep_795
Spiteller P, Jovanović J, Spiteller M. NMR analysis of (1S, 1aR, 6aR)-2’, 3’, 6, 6a-tetrahydrospiro cycloprop a indene-1(1aH), 1’- 1H indene. in Journal of the Serbian Chemical Society. 2005;70(10):1133-1136. https://hdl.handle.net/21.15107/rcub_technorep_795 .
Spiteller, Peter, Jovanović, Jovan, Spiteller, Michael, "NMR analysis of (1S, 1aR, 6aR)-2’, 3’, 6, 6a-tetrahydrospiro cycloprop a indene-1(1aH), 1’- 1H indene" in Journal of the Serbian Chemical Society, 70, no. 10 (2005):1133-1136, https://hdl.handle.net/21.15107/rcub_technorep_795 .