Substituted Diazatetracyclo[4.4.0.13,10.15,8]dodecanes as Stable Caged Proton Sponges
| Název česky | Substituované diazatetracyklo[4.4.0.13,10.15,8]dodekany jako stabilní klecovité protonové houby |
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| Autoři | |
| Rok publikování | 2012 |
| Druh | Článek v odborném periodiku |
| Časopis / Zdroj | The Journal of Organic Chemistry |
| Fakulta / Pracoviště MU | |
| Citace | |
| www | http://pubs.acs.org/doi/abs/10.1021/jo202235f |
| Doi | http://dx.doi.org/10.1021/jo202235f |
| Obor | Organická chemie |
| Klíčová slova | transprotonation - basicity - proton sponge - DTDs |
| Popis | 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 determined by transprotonation experiments as well as their sensitivity toward nucleophiles, acids and bases. Crystal structures of free base and monoprotonated form are discussed. |
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