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

Kód výsledku v 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>

Výsledek na webu

—

DOI - Digital Object Identifier

—

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

—

Projekt

—

Návaznosti

Z - Vyzkumny zamer (s odkazem do CEZ)

Rok uplatnění

2007

Kód důvěrnosti údajů

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

Název periodika

European Journal of Organic Chemistry

ISSN

1434-193X

e-ISSN

—

Svazek periodika

—

Číslo periodika v rámci svazku

30

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

11

Strana od-do

5101-5111

Kód UT WoS článku

—

EID výsledku v databázi Scopus

—