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APPLICATION OF NMR IN DETERMINING CYCLOADDITION PHOTOPRODUCTS STEREOCHEMISTRY

Excited state reactivity of various (hetero)aryl derivatives of o-divinyl-benzene, o-vinyl- butadienyl-benzene and o-dibutadienyl-benzene is of great importance as it gives a pathway to intramolecular polycyclic photoproducts that are taxing or even impossible to obtain via ground state synthetic organic chemistry approaches [1- 4]. It is also an interesting subject because of illustration of diverse photoproducts formed by introducing different substituents into the system. The resulting photoproducts have characteristic stereochemistry on some carbon atoms showing in NMR spectra specific recognizable values of coupling constants and interactions through space. The exact stereochemistry of photoproducts determined by NMR also can indicates the mechanism of reactions in the excited state [2, 4]. Additionally, star representatives of the group of photoproducts that were obtained possess the benzobicyclo-[3.2.1]octadiene skeleton which show promising biological activity [3]. REFERENCES [1] A. Ratković, M. Mlakić, W. Dehaen, T. Opsomer, D. Barić, I. Škorić, Spectrochim. Acta, Part A 2021, 261, 120056. [2] A. Grgičević, L. Fodor, D. Barić, M. Poje, Ž. Marinić, O. Horváth, I. Škorić, J. Photochem. Photobiol., A 2020, 400, 112690. [3] T. Čadež, A. Grgičević, R. Ahmetović, D. Barić, N. Maček Hrvat, Z. Kovarik, I. Škorić, Molecules, 2020, 25, 4872. [4] I. Šagud, M. Levačić, Ž. Marinić, I. Škorić, Eur. J. Org. Chem. 2017, 2017, 3787.

structure characterization, NMR, stereochemistry, intramolecular photoproducts

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