Synthesis of noradamantane derivatives by ring-contraction of the adamantane framework
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F21%3A10439245" target="_blank" >RIV/00216208:11310/21:10439245 - isvavai.cz</a>
Result on the web
<a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=~Y4XUaWSQU" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=~Y4XUaWSQU</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/d1ob00471a" target="_blank" >10.1039/d1ob00471a</a>
Alternative languages
Result language
angličtina
Original language name
Synthesis of noradamantane derivatives by ring-contraction of the adamantane framework
Original language description
We describe a triflic acid promoted cascade reaction of adamantane derivatives consisting of a decarboxylation of N-methyl protected cyclic carbamates and a subsequent intramolecular nucleophilic 1,2-alkyl shift to generate ring contracted iminium triflates. This reaction expands the family of similar transformations, such as Wagner-Meerwein-, Demjanov-Tiffeneau-, Meinwald- or (semi-)pinacol-rearrangement. It allows the preparation of noradamantane derivatives in a few steps, starting from simple hydroxy-substituted adamantane precursors.
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
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Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
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
Organic and Biomolecular Chemistry
ISSN
1477-0520
e-ISSN
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Volume of the periodical
19
Issue of the periodical within the volume
18
Country of publishing house
GB - UNITED KINGDOM
Number of pages
5
Pages from-to
4027-4031
UT code for WoS article
000640672800001
EID of the result in the Scopus database
2-s2.0-85105770314