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

Sohora, Margareta; Šumanovac Ramljak, Tatjana; Mlinarić-Majerski, Kata; Basarić, Nikola (2014) Photodecarboxylation of N-Adamantyl- and N-Phenylphthalimide Dipeptide Derivatives. Croatica chemica acta, 87 (4). pp. 431-446. ISSN 0011-1643

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Abstract

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.

Item Type: Article
Uncontrolled Keywords: Photodecarboxylation, Dipeptides, Phthalimides
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Division of Organic Chemistry and Biochemistry
Projects:
Project titleProject leaderProject codeProject type
Fotokemija policikličkih molekula: od istraživanja mehanizama reakcije do novih lijekova i medicinskih primjena[250000] Basarić NikolaUIP-02.05/25HRZZ
Kavezasti spojevi: ugradbene jedinice u molekularnim sustavima[27342] Kata Majerski098-0982933-2911MZOS
Depositing User: Sofija Konjević
Date Deposited: 10 Mar 2015 14:26
Last Modified: 05 May 2015 13:32
URI: http://fulir.irb.hr/id/eprint/1713
DOI: 10.5562/cca2482

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