Naslov
Photochemical generation of aza-o-quinone methides

Autori
Draženović, Josip ; Basarić, Nikola

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

Izvornik
28th PhotoIUPAC Symposium on Photochemistry : Book of abstracts / - , 2022, 236-236

Skup
28th IUPAC Symposium on Photochemistry

Mjesto i datum
Amsterdam, Nizozemska, 17.07.2022. - 22.07.2022

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
Photodehydration ; Photoelimination of acetic acid ; Aza-quinone methide

Sažetak
Aza-quinone methides (a-QM) are reactive intermediates, reacting with nucleophiles and various types of dienophiles, applicable in the synthesis of biologically important heterocycles. Due to their importance in synthesis, several methods to generate a-QM have been reported, including photogeneration from o-aminobenzyl alcohol. Although a-QM has been detected by laser flash photolysis (LFP), its trapping by alkenes in [4 + 2] cycloaddition in the acidic solution was hampered, and the composition of the irradiated mixture strongly depended on the solution pH. We conducted a systematic mofication of the structure of a-QM precursors in order to optimize the conditions for their photogeneration and enable trapping by alkenes. The amino group was functionalized by EWG, whereas the alcohol was converted to a better leaving group. The photoreactivity was investigated by irradiation experiments, and the products were isolated and fully characterized. To unravel details about the reaction mechanism, steady-state and time-resolved fluorescence and LFP measurements were conducted.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA