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[3+2] cycloaddition with photogenerated azomethine ylides in β-cyclodextrin


Margareta, Sohora; Mandić, Leo; Basarić, Nikola
[3+2] cycloaddition with photogenerated azomethine ylides in β-cyclodextrin // Beilstein journal of organic chemistry, 16 (2020), 1296-1304 doi:10.3762/bjoc.16.110 (međunarodna recenzija, članak, znanstveni)


Naslov
[3+2] cycloaddition with photogenerated azomethine ylides in β-cyclodextrin

Autori
Margareta, Sohora ; Mandić, Leo ; Basarić, Nikola

Izvornik
Beilstein journal of organic chemistry (2195-951X) 16 (2020); 1296-1304

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
[3 + 2] cycloadditions ; β-cyclodextrin ; inclusion complexes ; photochemistry ; phthalimides

Sažetak
Stability constants for the inclusion complexes of cyclohexylphthalimide 2 and adamantylphthalimide 3 with β-cyclodextrin (β-CD) were determined by 1H NMR titration, K = 190 ± 50 M-1, and K = 2600 ± 600 M-1, respectively. Photochemical reactivity of the inclusion complexes 2@β-CD and 3@β-CD was investigated, and we found out that β-CD does not affect the decarboxylation efficiency, while it affects the subsequent photochemical H-abstraction, resulting in different product distribution upon irradiation in the presence of β-CD. Formation of ternary complexes with acrylonitrile (AN) and 2@β-CD or 3@β-CD was also essayed by 1H NMR. Although formation of such complexes was suggested, stability constants could not be determined. Irradiation of 2@β-CD in the presence of AN in aqueous solution where cycloadduct 7 was formed highly suggests that decarboxylation and [3+2] cycloaddition take place in the ternary complex, whereas such a reactivity from bulky adamantane 3 is less likely. This proof of principle that decarboxylation and cycloaddition can be performed in the β-CD cavity has a significant importance for the design of new supramolecular systems for the control of photoreactivity.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
HRZZ-IP-2014-09-6312 - Supramolekulska kontrola fotokemijskih reakcija eliminacije (Nikola Basarić, )

Ustanove
Institut "Ruđer Bošković", Zagreb

Profili:

Avatar Url Nikola Basarić (autor)

Avatar Url Leo Mandić (autor)

Avatar Url Margareta Sohora (autor)

Citiraj ovu publikaciju

Margareta, Sohora; Mandić, Leo; Basarić, Nikola
[3+2] cycloaddition with photogenerated azomethine ylides in β-cyclodextrin // Beilstein journal of organic chemistry, 16 (2020), 1296-1304 doi:10.3762/bjoc.16.110 (međunarodna recenzija, članak, znanstveni)
Margareta, S., Mandić, L. & Basarić, N. (2020) [3+2] cycloaddition with photogenerated azomethine ylides in β-cyclodextrin. Beilstein journal of organic chemistry, 16, 1296-1304 doi:10.3762/bjoc.16.110.
@article{article, year = {2020}, pages = {1296-1304}, DOI = {10.3762/bjoc.16.110}, keywords = {[3 + 2] cycloadditions, β-cyclodextrin, inclusion complexes, photochemistry, phthalimides}, journal = {Beilstein journal of organic chemistry}, doi = {10.3762/bjoc.16.110}, volume = {16}, issn = {2195-951X}, title = {[3+2] cycloaddition with photogenerated azomethine ylides in β-cyclodextrin}, keyword = {[3 + 2] cycloadditions, β-cyclodextrin, inclusion complexes, photochemistry, phthalimides} }

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus


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