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PPhotocycloaddition reactions: excited state transformations of heterostilbenes to polycyclic skeleta

For the past 40 years Professor M. Šindler- Kulyk’s group has been studying excited state reactivity of various heteroaromatic analogues of o-vinylstilbenes, o-vinylstyryl- and o- phenylenedivinylene-aromatic heterocycles, simply called o-vinyl- heterostilbenes and di- heterostilbenes. This is a concise overview of a vast research focusing on photocycloaddition reactions. To this date furan, pyrrole, sydnone, thiophene, oxazole and most lately pyridine nuclei were incorporated into the basic stilbene-type skeleton. The photocycloaddition reactions of these compounds are of great importance as they give a pathway to new polycyclic products that are taxing or even impossible to obtain via ground state synthetic organic chemistry approaches. It is also an interesting subject because of the diverse photocycloadducts formed by introducing different substituents into the system were the conformation and electronic distribution in the molecule changes as a consequence. As star representatives of the group of polycyclic structures that were obtained are the benzobicyclo[3.2.1]octadiene photoproducts which are showing promising biological activity.

benzobicyclo[3.2.1]octadiene, excited state reactions, heterostilbenes, photocycloadditions, polycycles

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