Application of PhSCF2CF2SiMe3 as a Tandem Anion and Radical Tetrafluoroethylene Equivalent: Fluoride-Catalyzed Addition to N-Substituted Cyclic Imides Followed by Radical Cyclization

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F12%3A00376746" target="_blank" >RIV/61388963:_____/12:00376746 - isvavai.cz</a>

Result on the web

<a href="http://dx.doi.org/10.1055/s-0031-1290917" target="_blank" >http://dx.doi.org/10.1055/s-0031-1290917</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1055/s-0031-1290917" target="_blank" >10.1055/s-0031-1290917</a>

Result language

angličtina

Original language name

Application of PhSCF2CF2SiMe3 as a Tandem Anion and Radical Tetrafluoroethylene Equivalent: Fluoride-Catalyzed Addition to N-Substituted Cyclic Imides Followed by Radical Cyclization

Original language description

PhSCF2CF2SiMe3 undergoes a fluoride-catalyzed nucleophilic addition to N-substituted cyclic amides affording adducts in moderate to good yields. Reductive cleavage of the phenylsulfanyl group of N-methylated adducts under radical conditions yields the corresponding tetrafluoroethyl-containing adducts in excellent yields. Under the same reduction conditions, N-allylated adducts undergo 6-exo radical cyclization to afford the corresponding tetrafluorinated 1-azabicyclic compounds in moderate to good yields and cis selectivities.

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

<a href="/en/project/GAP207%2F11%2F0421" target="_blank" >GAP207/11/0421: Nucleophilic and radical tetrafluoroethyl and tetrafluoroethylene group transfer.</a><br>

Continuities

Z - Vyzkumny zamer (s odkazem do CEZ)

Publication year

2012

Confidentiality

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

Name of the periodical

Synlett

ISSN

0936-5214

e-ISSN

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Volume of the periodical

23

Issue of the periodical within the volume

8

Country of publishing house

DE - GERMANY

Number of pages

4

Pages from-to

1187-1190

UT code for WoS article

000303654100008

EID of the result in the Scopus database

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