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Photoinduced hydrogen atom abstraction in N-(adamantyl)phthalimides: Structure-Reactivity Study in the Solid State


Basarić, Nikola; Horvat, Margareta; Franković, Oliver; Mlinarić-Majerski, Kata; Neudörfl, Jörg; Griesbeck, Axel G.
Photoinduced hydrogen atom abstraction in N-(adamantyl)phthalimides: Structure-Reactivity Study in the Solid State // Tetrahedron, 65 (2009), 7; 1438-1443 doi:10.1016/j.tet.2008.10.010 (međunarodna recenzija, članak, znanstveni)


Naslov
Photoinduced hydrogen atom abstraction in N-(adamantyl)phthalimides: Structure-Reactivity Study in the Solid State

Autori
Basarić, Nikola ; Horvat, Margareta ; Franković, Oliver ; Mlinarić-Majerski, Kata ; Neudörfl, Jörg ; Griesbeck, Axel G.

Izvornik
Tetrahedron (0040-4020) 65 (2009), 7; 1438-1443

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

Ključne riječi
Adamantane phthalimides; photoinduced H abstraction; solid state photochemistry; X-ray analysis

Sažetak
Adamantyl-functionalized phthalimides were synthesized and the probability of intramolecular photochemical hydrogen atom abstraction in the solid-state analyzed by X-ray crystallographic analyses. These analyses and solid-state photolyses showed that the parameters determining photochemical reactivity for typical carbonyl compounds in the solid state can also be extended to phthalimides. Only N-(2-adamantyl)phthalimide underwent a solid state photochemical reaction, which is the first example in the phthalimide series. This reaction is regio- and stereoselective, resulting in an endo-alcohol. On the other hand, the photoreaction of N-(2-adamantyl)phthalimide in solution gives an exo-alcohol as the main product together with an endo-alcohol and a benzazepindione.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
098-0982933-2911 - Kavezasti spojevi: ugradbene jedinice u molekularnim sustavima (Kata Majerski, )

Ustanove
Institut "Ruđer Bošković", Zagreb

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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