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Photodecarboxylation of amino acids activated by phthalimide


Mandić, Leo; Mlinarić-Majerski, Kata; Basarić, Nikola
Photodecarboxylation of amino acids activated by phthalimide // E-WISPOC 2015 / Chemistry and Chemical Processes in Confined Spaces
Bressanone, 2015. str. 65-65 (poster, međunarodna recenzija, sažetak, znanstveni)


Naslov
Photodecarboxylation of amino acids activated by phthalimide

Autori
Mandić, Leo ; Mlinarić-Majerski, Kata ; Basarić, Nikola

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
E-WISPOC 2015 / Chemistry and Chemical Processes in Confined Spaces / - Bressanone, 2015, 65-65

Skup
E-WISPOC 2015 / Chemistry and Chemical Processes in Confined Spaces

Mjesto i datum
Bressanone, Italija, 11-6.2.2015

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
Photochemistry; supramolecular chemistry; azomethine ylides

Sažetak
Azomethine ylides are 1, 3-dipoles which can be generated from many sources, including aziridines, imines, and iminiums.1 Another way of azomethine ylide generation, which attracted our attention, is photochemical decarboxylation reaction of N-phthaloyl α-amino acids.2 For example, irradiation of N-phthaloylglycine (1) in acetonitrile generates azomethine ylide 1-AY, which subsequently undergo [3+2] reaction with acrylonitrile to form cycloadducts 2, along with formation of N-methylphthalimide (3). Within the scope of our investigation on photodecarboxylation of amino acids derived from different cage molecules and activated with phthalimide chromophore, 3 we turned our attention to potential [3+2] cycloaddition with phthalimide derivatives 4 and 5. However, preliminary photochemical reactions of 4 and 5 in solution in the presence of acrylonitrile gave only simple decarboxylation products. To circumvent this problem, it is planned to use supramolecular control of the photochemical reaction. Complexation of 1, 4 and 5 with various macrocyclic hosts, such as cyclodextrins and cucurbit[n]urils, is anticipated to enable [3+2] cycloadditions with photochemically generated azomethine ylides.

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