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Photodecarboxylation of N-Adamantyl- and N-Phenylphthalimide Dipeptide Derivatives


Sohora, Margareta; Šumanovac Ramljak, Tatjana; Mlinarić-Majerski, Kata; Basarić, Nikola
Photodecarboxylation of N-Adamantyl- and N-Phenylphthalimide Dipeptide Derivatives // Croatica chemica acta, 87 (2014), 4; 431-446 doi:10.5562/cca2482 (međunarodna recenzija, članak, znanstveni)


Naslov
Photodecarboxylation of N-Adamantyl- and N-Phenylphthalimide Dipeptide Derivatives

Autori
Sohora, Margareta ; Šumanovac Ramljak, Tatjana ; Mlinarić-Majerski, Kata ; Basarić, Nikola

Izvornik
Croatica chemica acta (0011-1643) 87 (2014), 4; 431-446

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

Ključne riječi
Photodecarboxylation; dipeptides; phthalimides

Sažetak
New dipeptide derivatives 1 and 3 were synthesized and their reactivity in the photochemical reaction of decarboxylation was investigated. The photodecarboxylation of N-adamantyl derivatives 1a and 1b and N-phenylphthalimide derivatives 3a and 3b probably takes place from the triplet excited state. The triplet excited state of 1a, 3a and 3b was characterized by laser flash photolysis. N-phenylphthalimides 3a and 3b undergo 2-5 times more efficient photodecarboxylation than N-adamantylphthalimides 1a and 1b. The aminoacid residue (Phe or Gly) at the C-terminus of the dipeptide does not influence the photodecarboxylation efficiency. Product selectivity in the photoreactions is determined by the conformation of the molecules. N-phenylphthalimides with the separated electron donor (carboxylate) and acceptor moiety (phthalimide) give only simple decarboxylation products, whereas N-adamantyl derivatives also give cyclization products.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
02.05/25
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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