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  • Herein, we report a molecular framework design differing significantly from the traditional topology of proton sponges. We developed a suitable synthetic approach to the preparation of compounds with four fused five-membered rings from homoallenyl aldehydes by intramolecular criss-cross cycloaddition reactions of appropriate homoallenyl azines. The acid-catalyzed rearrangement of these cycloadducts afforded caged bidentate secondary amines in quantitative yields and following alkylation reactions led to final air nonsensitive highly stable substituted diazatetracyclo[4.4.0.13,10.15,8]dodecanes (DTDs) with rare alicyclic scaffolding in high overall yields. These molecules have two pairs of nitrogen atoms fixed in a configuration that guarantees acid-base properties similar to those of proton sponges. Their pKBH+ values were determined by 1H NMR transprotonation experiments as well as their sensitivity toward nucleophiles, acids and bases.
  • Herein, we report a molecular framework design differing significantly from the traditional topology of proton sponges. We developed a suitable synthetic approach to the preparation of compounds with four fused five-membered rings from homoallenyl aldehydes by intramolecular criss-cross cycloaddition reactions of appropriate homoallenyl azines. The acid-catalyzed rearrangement of these cycloadducts afforded caged bidentate secondary amines in quantitative yields and following alkylation reactions led to final air nonsensitive highly stable substituted diazatetracyclo[4.4.0.13,10.15,8]dodecanes (DTDs) with rare alicyclic scaffolding in high overall yields. These molecules have two pairs of nitrogen atoms fixed in a configuration that guarantees acid-base properties similar to those of proton sponges. Their pKBH+ values were determined by 1H NMR transprotonation experiments as well as their sensitivity toward nucleophiles, acids and bases. (en)
Title
  • From homoallenyl aldehydes to proton sponges
  • From homoallenyl aldehydes to proton sponges (en)
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  • From homoallenyl aldehydes to proton sponges
  • From homoallenyl aldehydes to proton sponges (en)
skos:notation
  • RIV/00216224:14310/12:00057492!RIV13-GA0-14310___
http://linked.open...avai/predkladatel
http://linked.open...avai/riv/aktivita
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  • P(GA203/09/1345)
http://linked.open...vai/riv/dodaniDat
http://linked.open...aciTvurceVysledku
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  • 137298
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  • RIV/00216224:14310/12:00057492
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  • allenyl aldehyde - rearrangement - proton sponge - basicity (en)
http://linked.open.../riv/klicoveSlovo
http://linked.open...ontrolniKodProRIV
  • [9A587656FACF]
http://linked.open...in/vavai/riv/obor
http://linked.open...ichTvurcuVysledku
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http://linked.open...vavai/riv/projekt
http://linked.open...UplatneniVysledku
http://linked.open...iv/tvurceVysledku
  • Galeta, Juraj
  • Potáček, Milan
http://localhost/t...ganizacniJednotka
  • 14310
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