Naslov
Photochemical Approach to Heteropolycyclic Compounds

Autori
Šindler-Kulyk, Marija ; Basarić, Nikola

Izvornik
Kemija u industriji (0022-9830) 51 (2002), 4; 169-175

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, pregledni rad, znanstveni

Ključne riječi
photochemistry; cycloaddition; heterocycles; stilbene; furan; pyrrole; polycycles

Sažetak
Heterocyclic stilbene analogues, furan, benzofuran, naphthofuran as well as pyrrole derivatives of o-divinylbenzene, are useful substrates for the photochemical transformations to the heteropolycyclic compounds in one step. While furan and benzofuran derivatives give bicyclo[3.2.1]octadiene structures by intramolecular cycloaddition and heterocyclic ring participation, the naphthofuran analogues give cyclobutane products, formed by [2+2] intermolecular cycloaddition. Nitrogen analogues, with pyrrole ring as a substituent, behave completely different, giving dimeric products by intermolecular pyrrole addition to the double bond. The mechanism includes electron transfer followed by hydrogen transfer and radical combination. When both vinyl groups in o-divinylbenzene are substituted with a pyrrole moiety the main process is, after an electron transfer and hydrogen transfer, the intramolecular ring closure to indane derivatives followed by the second inter- or intramolecular reaction with pyrrole.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA