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Statements

Subject Item
n2:RIV%2F60461373%3A22310%2F07%3A00018534%21RIV08-MSM-22310___
rdf:type
n4:Vysledek skos:Concept
dcterms:description
3-Fluorofuran-2(5H)-one (1) and three 3,4-difluorofuran-2(5H)-ones 2-4, α,β-unsaturated lactones possessing fluorinateddouble bonds, were applied as dienophiles in Diels-Alder reactions with normal electron demand using diphenylisobenzofuran or cyclopentadiene as dienes. In the same reactions, furan or 2,3-dimethylbuta-1,3-diene were completely unreactive. Three structural factors of furan-2(5H)-ones appeared to have an effect on the reactivity, regioselectivity and diastereoselectivity of the [4+2] cycloadditions: the number of fluorine atoms attached to the double bond and the number and the bulkiness of alkyl substituents at the 5-position of the furan-2(5H)-one system. The monofluorinated furan-2(5H)-one 1 was generally more reactive than the difluorinated furan-2(5H)-ones 2-4. While the reactions of the furan-2(5H)-ones 2-4 with isobenzofuran exclu-sively gave exo products, those of the monofluorinated lactone 1 led to mixtures of endo and exo diastereoisomeric [4+2] cycloadducts. All 3-Fluorfuran-2(5H)-on (1) a tři 3,4-difluorfuran-2(5H)-ony 2-4, α,β-nenasycené laktony s fluorovanými dvojnými vazbami, byly využity jako dienofily v Diels-Alderových reakcích s normálními elektronickými požadavky s využitím difenylisobenzofuranu nebo cyklopentadienu jako dienů. 3-Fluorofuran-2(5H)-one (1) and three 3,4-difluorofuran-2(5H)-ones 2-4, α,β-unsaturated lactones possessing fluorinateddouble bonds, were applied as dienophiles in Diels-Alder reactions with normal electron demand using diphenylisobenzofuran or cyclopentadiene as dienes. In the same reactions, furan or 2,3-dimethylbuta-1,3-diene were completely unreactive. Three structural factors of furan-2(5H)-ones appeared to have an effect on the reactivity, regioselectivity and diastereoselectivity of the [4+2] cycloadditions: the number of fluorine atoms attached to the double bond and the number and the bulkiness of alkyl substituents at the 5-position of the furan-2(5H)-one system. The monofluorinated furan-2(5H)-one 1 was generally more reactive than the difluorinated furan-2(5H)-ones 2-4. While the reactions of the furan-2(5H)-ones 2-4 with isobenzofuran exclu-sively gave exo products, those of the monofluorinated lactone 1 led to mixtures of endo and exo diastereoisomeric [4+2] cycloadducts. All
dcterms:title
Fluorované furan-2(5H)-ony: reaktivita a stereoselektivit a v Diels-Alderových reakcích Fluorinated furan-2(5H)-ones: reactivity and stereoselectivity in Diels-Alder reactions Fluorinated furan-2(5H)-ones: reactivity and stereoselectivity in Diels-Alder reactions
skos:prefLabel
Fluorované furan-2(5H)-ony: reaktivita a stereoselektivit a v Diels-Alderových reakcích Fluorinated furan-2(5H)-ones: reactivity and stereoselectivity in Diels-Alder reactions Fluorinated furan-2(5H)-ones: reactivity and stereoselectivity in Diels-Alder reactions
skos:notation
RIV/60461373:22310/07:00018534!RIV08-MSM-22310___
n3:strany
5101-5111
n3:aktivita
n6:Z
n3:aktivity
Z(MSM6046137301)
n3:cisloPeriodika
30
n3:dodaniDat
n10:2008
n3:domaciTvurceVysledku
n8:1903357 n8:1982346 n8:4589181
n3:druhVysledku
n16:J
n3:duvernostUdaju
n9:S
n3:entitaPredkladatele
n7:predkladatel
n3:idSjednocenehoVysledku
422268
n3:idVysledku
RIV/60461373:22310/07:00018534
n3:jazykVysledku
n12:eng
n3:klicovaSlova
Cycloaddition / DFT calculations / Diels-Alder reactions / Fluorinated heterocycles / Lactones
n3:klicoveSlovo
n18:Cycloaddition%20%2F%20DFT%20calculations%20%2F%20Diels-Alder%20reactions%20%2F%20Fluorinated%20heterocycles%20%2F%20Lactones
n3:kodStatuVydavatele
DE - Spolková republika Německo
n3:kontrolniKodProRIV
[F5220F8FAD26]
n3:nazevZdroje
European Journal of Organic Chemistry
n3:obor
n13:CC
n3:pocetDomacichTvurcuVysledku
3
n3:pocetTvurcuVysledku
4
n3:rokUplatneniVysledku
n10:2007
n3:tvurceVysledku
Kvíčala, Jaroslav Hajduch, Jan Paleta, Oldřich Haufe, Günter
n3:zamer
n15:MSM6046137301
s:issn
1434-193X
s:numberOfPages
11
n17:organizacniJednotka
22310