About: Hydroboration of 1,1′-bi(cyclopent-1-ene) and 3,3′-biindene: experimental and theoretical study

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About: Hydroboration of 1,1′-bi(cyclopent-1-ene) and 3,3′-biindene: experimental and theoretical study Goto Sponge Distinct Permalink

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	Hydroborace bi(cyklopent-1-enu) (1) nebo 3,3′-biindenu (2) s boranem, thexylboranem nebo (-)-isopinokamfeylboranem poskytla bez ohledu na reakční podmínky meso-isomery polycyklických 1,4-diolů 3a, 4a jako hlavní produkty. 9-BBN nereagoval. Struktura hlavního produktu4a a vedlejšího racemického produktu 4b byly určeny pomocí 1H NMR spekter odpovídajících Mosherových diesterů 5a-5c. Stereochemie produktu 4a byla potvrzena krystalografickou analýzou odpovídajícího dimesylátu 6. Za účelem vysvětlení přednostního vzniku meso-isomerů byly komplexy monohydroborovanýchz intermediatů s borany studovány teoreticky pomocí DFT method. (cs) Hydroboration of bi(cyclopent-1-ene) (1) or 3,3′-biindene (2) with borane, thexylborane or (-)-isopinocampheylborane afforded, regardless of reaction conditions, meso-isomers of polycyclic 1,4-diols 3a, 4a as the main products. No reaction was observed with 9-BBN. The structure of the major product 4a, as well as of the minor racemic product 4b was assigned based on 1H NMR spectra of the corresponding Mosher's diesters 5a-5c. Finally, the stereochemistry of the product 4a was confirmed by a single-crystal X-ray analysis of the corresponding dimesylate 6. To elucidate preferential formation of the meso-isomers, complexes of monohydroborated intermediate with borane were studied theoretically by DFT methods. Hydroboration of bi(cyclopent-1-ene) (1) or 3,3′-biindene (2) with borane, thexylborane or (-)-isopinocampheylborane afforded, regardless of reaction conditions, meso-isomers of polycyclic 1,4-diols 3a, 4a as the main products. No reaction was observed with 9-BBN. The structure of the major product 4a, as well as of the minor racemic product 4b was assigned based on 1H NMR spectra of the corresponding Mosher's diesters 5a-5c. Finally, the stereochemistry of the product 4a was confirmed by a single-crystal X-ray analysis of the corresponding dimesylate 6. To elucidate preferential formation of the meso-isomers, complexes of monohydroborated intermediate with borane were studied theoretically by DFT methods. (en)
Title	Hydroboration of 1,1′-bi(cyclopent-1-ene) and 3,3′-biindene: experimental and theoretical study Hydroborace 1,1′-bi(cyklopent-1-enu) a 3,3′-biindenu: experimentální a teoretická studie (cs) Hydroboration of 1,1′-bi(cyclopent-1-ene) and 3,3′-biindene: experimental and theoretical study (en)
skos:prefLabel	Hydroboration of 1,1′-bi(cyclopent-1-ene) and 3,3′-biindene: experimental and theoretical study Hydroborace 1,1′-bi(cyklopent-1-enu) a 3,3′-biindenu: experimentální a teoretická studie (cs) Hydroboration of 1,1′-bi(cyclopent-1-ene) and 3,3′-biindene: experimental and theoretical study (en)
skos:notation	RIV/60461373:22310/06:00017028!RIV07-MSM-22310___
http://linked.open.../vavai/riv/strany	1611-1626
http://linked.open...avai/riv/aktivita	P Z
http://linked.open...avai/riv/aktivity	P(GA203/03/0496), Z(MSM6046137301)
http://linked.open...iv/cisloPeriodika	11-12
http://linked.open...vai/riv/dodaniDat	2007
http://linked.open...aciTvurceVysledku	Krupková, Alena Kvíčala, Jaroslav Stránská, Denisa
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Vysoká škola chemicko-technologická v Praze / Fakulta chemické technologie
http://linked.open...dnocenehoVysledku	478506
http://linked.open...ai/riv/idVysledku	RIV/60461373:22310/06:00017028
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	Dienes; Asymmetric hydroboration; Boranes; Chiral diols; Mosher's esters; Absolute configuration; DFT calculations; X-ray diffraction. (en)
http://linked.open.../riv/klicoveSlovo	Boranes Dienes X-ray diffraction. DFT calculations Absolute configuration Asymmetric hydroboration Chiral diols Mosher's esters
http://linked.open...odStatuVydavatele	CZ - Česká republika
http://linked.open...ontrolniKodProRIV	[2E0CC8C78B6C]
http://linked.open...i/riv/nazevZdroje	Collection of Czechoslovak Chemical Communications
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	3 (xsd:int)
http://linked.open...cetTvurcuVysledku	4 (xsd:int)
http://linked.open...vavai/riv/projekt	Chiral 7-bora- and 7-silabicyclo[6.3.0.0]undecanes and their benzo analogues. Syntheses and applications
http://linked.open...UplatneniVysledku	2006
http://linked.open...v/svazekPeriodika	71
http://linked.open...iv/tvurceVysledku	Baszczyňski, Ondřej Krupková, Alena Kvíčala, Jaroslav Stránská, Denisa
http://linked.open...n/vavai/riv/zamer	Catalytic processes in chemistry and chemical technology
issn	0010-0765
number of pages	16 (xsd:int)
http://localhost/t...ganizacniJednotka	22310
is http://linked.open...avai/riv/vysledek of	Hydroboration of 1,1′-bi(cyclopent-1-ene) and 3,3′-biindene: experimental and theoretical study Hydroboration of 1,1′-bi(cyclopent-1-ene) and 3,3′-biindene: experimental and theoretical study

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About: Hydroboration of 1,1&#8242;-bi(cyclopent-1-ene) and 3,3&#8242;-biindene: experimental and theoretical study Goto Sponge Distinct Permalink

About: Hydroboration of 1,1′-bi(cyclopent-1-ene) and 3,3′-biindene: experimental and theoretical study Goto Sponge Distinct Permalink