Substituted Diazatetracyclo[4.4.0.13,10.15,8]dodecanes as Stable Caged Proton Sponges

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14310%2F12%3A00057241" target="_blank" >RIV/00216224:14310/12:00057241 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1021/jo202235f" target="_blank" >http://dx.doi.org/10.1021/jo202235f</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/jo202235f" target="_blank" >10.1021/jo202235f</a>

Result language
angličtina
Original language name
Substituted Diazatetracyclo[4.4.0.13,10.15,8]dodecanes as Stable Caged Proton Sponges
Original language description
Herein, we report a molecular framework design differing significantly from the traditional topology of proton sponges. We developed a synthetic approach to the preparation of caged secondary amines by acid-catalyzed rearrangement of fused tetracyclic heterocycles synthesized by intramolecular criss-cross cycloaddition. Alkylation of amines led to air nonsensitive diazatetracyclo[4.4.0.13,10.15,8]dodecanes (DTDs) with rare alicyclic scaffolding in high overall yields. Their pKBH+ values were determinedby transprotonation experiments as well as their sensitivity toward nucleophiles, acids and bases. Crystal structures of free base and monoprotonated form are discussed.
Czech name
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Czech description
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Type
J<sub>x</sub> - 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/GA203%2F09%2F1345" target="_blank" >GA203/09/1345: Allenyl synthon in synthesis of heterocyclic compounds</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2012
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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