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 NotDistinct Permalink

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	Hydroboration of bi(cyclopent-1-ene) and 3,3'-biindene with borane, thexylborane or (–)-isopinocampheylborane afforded, regardless of reaction conditions, meso-isomers of the corresponding diols as the main products. No reaction was observed with 9-BBN. The structure of both major and minor isomer of 1,1'-biindane-2,2'-diol was assigned on the basis of 1H NMR spectra of the corresponding Mosher’s diesters. The stereochemistry of the meso-isomer of 1,1'-biindane-2,2'-diol was confirmed by a single-crystal X-ray analysis of the corresponding dimesylate. To explain the observed stereoselectivity, a theoretical study of the complexes of monohydroborated intermediate with borane was made using DFT methods. Hydroboration of bi(cyclopent-1-ene) and 3,3'-biindene with borane, thexylborane or (–)-isopinocampheylborane afforded, regardless of reaction conditions, meso-isomers of the corresponding diols as the main products. No reaction was observed with 9-BBN. The structure of both major and minor isomer of 1,1'-biindane-2,2'-diol was assigned on the basis of 1H NMR spectra of the corresponding Mosher’s diesters. The stereochemistry of the meso-isomer of 1,1'-biindane-2,2'-diol was confirmed by a single-crystal X-ray analysis of the corresponding dimesylate. To explain the observed stereoselectivity, a theoretical study of the complexes of monohydroborated intermediate with borane was made using DFT methods. (en) Hydroborace bi(cyklopent-1-en)u a 3,3'-biindenu boranem, thexylboranem nebo (–)-isopinocampheylboranem poskytla bez ohledu na reakční podmínky meso-izomery odpovídajících diolů jako hlavní produkt. V případě 9-BBN nebyla pozorována žádná reakce. Struktura jak majoritního, tak minoritního izomeru 1,1'-biindan-2,2'-diolu byla určena na základě 1H NMR spekter odpovídajících Mosherových diesterů. Stereochemie meso-izomeru 1,1'-biindan-2,2'-diolu byla potvrzena rentgenovou strukturní analýzou odpovídajícího dimesylátu. Pro objasnění pozorované stereoselektivity byla provedena teoretická studie komplexů monohydroborovaných intermediátů s boranem metodami DFT. (cs)
Title	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. (en) Hydroborace 1,1'-bi(cyklopent-1-en)u a 3,3'-biindenu: experimentální a teoretická studie. (cs)
skos:prefLabel	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. (en) Hydroborace 1,1'-bi(cyklopent-1-en)u a 3,3'-biindenu: experimentální a teoretická studie. (cs)
skos:notation	RIV/67985858:_____/06:00315817!RIV09-AV0-67985858
http://linked.open...avai/riv/aktivita	Z
http://linked.open...avai/riv/aktivity	Z(AV0Z40720504)
http://linked.open...iv/cisloPeriodika	11-12
http://linked.open...vai/riv/dodaniDat	2009
http://linked.open...aciTvurceVysledku	Krupková, Alena
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	Ústav chemických procesů AV ČR, v. v. i.
http://linked.open...dnocenehoVysledku	478505
http://linked.open...ai/riv/idVysledku	RIV/67985858:_____/06:00315817
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	asymmetric hydroboration; dienes; dft calculations (en)
http://linked.open.../riv/klicoveSlovo	dienes asymmetric hydroboration dft calculations
http://linked.open...odStatuVydavatele	CZ - Česká republika
http://linked.open...ontrolniKodProRIV	[01518AE5E415]
http://linked.open...i/riv/nazevZdroje	Collection of Czechoslovak Chemical Communications
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	1 (xsd:int)
http://linked.open...cetTvurcuVysledku	4 (xsd:int)
http://linked.open...UplatneniVysledku	2006
http://linked.open...v/svazekPeriodika	71
http://linked.open...iv/tvurceVysledku	Krupková, Alena Kvíčala, J. Stránská, D. Baszczyňski, O.
http://linked.open...ain/vavai/riv/wos	000243130800008
http://linked.open...n/vavai/riv/zamer	Investigation of multiphase reacting systems for the design of processes important in synthesis and preparation of novel materials, in energy production and in environmental protection
issn	0010-0765
number of pages	16 (xsd:int)
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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