Fluorinated furan-2(5H)-ones: reactivity and stereoselectivity in Diels-Alder reactions

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F07%3A00018534" target="_blank" >RIV/60461373:22310/07:00018534 - isvavai.cz</a>

Result on the web

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DOI - Digital Object Identifier

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Result language

angličtina

Original language name

Fluorinated furan-2(5H)-ones: reactivity and stereoselectivity in Diels-Alder reactions

Original language description

3-Fluorofuran-2(5H)-one (1) and three 3,4-difluorofuran-2(5H)-ones 2-4, ?,?-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.

Czech name

Fluorované furan-2(5H)-ony: reaktivita a stereoselektivit a v Diels-Alderových reakcích

Czech description

3-Fluorfuran-2(5H)-on (1) a tři 3,4-difluorfuran-2(5H)-ony 2-4, ?,?-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.

Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

CC - Organic chemistry

OECD FORD branch

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Project

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Continuities

Z - Vyzkumny zamer (s odkazem do CEZ)

Publication year

2007

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

European Journal of Organic Chemistry

ISSN

1434-193X

e-ISSN

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Volume of the periodical

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Issue of the periodical within the volume

30

Country of publishing house

DE - GERMANY

Number of pages

11

Pages from-to

5101-5111

UT code for WoS article

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EID of the result in the Scopus database

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