Synthesis of 5-alkyl-3,4-difluorofuran-2(5H)-ones by lactonisation. Effects of substituents on cyclisation ability of fluorinated 4-hydroxyalkanoates. DFT calculations of the cyclisation energies

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F14%3A00429658" target="_blank" >RIV/61388963:_____/14:00429658 - isvavai.cz</a>

Result on the web

<a href="http://dx.doi.org/10.1016/j.jfluchem.2014.03.009" target="_blank" >http://dx.doi.org/10.1016/j.jfluchem.2014.03.009</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.jfluchem.2014.03.009" target="_blank" >10.1016/j.jfluchem.2014.03.009</a>

Result language

angličtina

Original language name

Synthesis of 5-alkyl-3,4-difluorofuran-2(5H)-ones by lactonisation. Effects of substituents on cyclisation ability of fluorinated 4-hydroxyalkanoates. DFT calculations of the cyclisation energies

Original language description

5-Alkyl-3,4-difluorofuran-2(5H)-ones were synthesised starting with radical addition of ethers to methyl 2,3,3-trifluoroprop-2-enoate, followed by alkyloxy bond cleavage, acid-catalyzed lactonisation and dehydrofluorination. For a study of substituent effects on lactonisation, methyl 4-bromo-2-chloro-2-fluorodecanoate and 2-chloro-2-fluoro-4,4-dimethoxybutanoate based on radical additions of methyl 2-bromo-2-chloro-2-fluoroacetate to oct-1-ene or vinyl acetate were prepared. DFT calculations of the transition state energies of the exo-trig cyclisations confirmed the observation that the ring closure became more feasible with increasing number of alkyls at C4 of the fluorinated 4-hydroxyesters.

Czech name

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Czech description

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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

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2014

Confidentiality

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

Name of the periodical

Journal of Fluorine Chemistry

ISSN

0022-1139

e-ISSN

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Volume of the periodical

162

Issue of the periodical within the volume

Jun

Country of publishing house

CH - SWITZERLAND

Number of pages

15

Pages from-to

45-59

UT code for WoS article

000336827000007

EID of the result in the Scopus database

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