Polyhalogenated Bicyclo[1.1.1]pentane-1,3-dicarboxylic Acids
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F21%3A00544534" target="_blank" >RIV/61388963:_____/21:00544534 - isvavai.cz</a>
Alternative codes found
RIV/00216208:11310/21:10430496
Result on the web
<a href="https://doi.org/10.1021/acs.joc.1c01020" target="_blank" >https://doi.org/10.1021/acs.joc.1c01020</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acs.joc.1c01020" target="_blank" >10.1021/acs.joc.1c01020</a>
Alternative languages
Result language
angličtina
Original language name
Polyhalogenated Bicyclo[1.1.1]pentane-1,3-dicarboxylic Acids
Original language description
Herein we report the highly selective radical chlorination of 2,2-difluorobicyclo[1.1.1]pentane-1,3-dicarboxylic acid. Together with radical hydrodechlorination by TMS3SiH, four new bicyclo[1.1.1]pentane cages carrying two fluorine and one to three chlorine atoms in bridge positions have been obtained. The exact positions of all halogen atoms have been confirmed by X-ray diffraction. The acidity constants (pKa) for all new derivatives have been determined by capillary electrophoresis, and these experimental values show excellent agreement with pKas predicted by DFT methods. Extensive DFT calculations have been used to rationalize the selective formation of four out of nine possible F2Cl1–4 isomers of bridge-halogenated bicyclo[1.1.1]pentanes and to obtain relative strain energies for all possible isomers.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2021
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Journal of Organic Chemistry
ISSN
0022-3263
e-ISSN
1520-6904
Volume of the periodical
86
Issue of the periodical within the volume
15
Country of publishing house
US - UNITED STATES
Number of pages
17
Pages from-to
10303-10319
UT code for WoS article
000684025500029
EID of the result in the Scopus database
2-s2.0-85111201485