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Photochemical approach to new polycyclic substrates suitable for further photocatalytic functionalization

Vuk, Dragana; Marinić, Željko; Škorić, Irena (2014) Photochemical approach to new polycyclic substrates suitable for further photocatalytic functionalization. Croatica chemica acta, 87 (4). pp. 465-473. ISSN 0011-1643

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Abstract

New polycyclic compounds are synthesized by photocycloaddition reactions of methoxy, methyl or phenyl substituted butadiene derivatives 11-14. Mono- and dimethoxy butadiene derivatives 11 and 12 undergo intramolecular [2+2] photocycloaddition giving benzobicyclo[3.2.1]octadiene structures (endo-15, endo, trans-17) as main products. As minor photoproducts tricyclic compounds endo-16 and endo, trans-18 are isolated, respectively, formed by [4+2] photoinduced cycloaddition of the starting molecules. The reaction of compounds 13 and 14 is more selective and only benzobicyclo[3.2.1]octadienes endo, endo-19 and endo, endo-20 are formed, respectively. New bicyclo[3.2.1]octadienes with isolated double bond can be suitable substrates for further efficient photocatalytic oxygenations in course of new functionalized polycycles, potentially more biologically active compounds.

Item Type: Article
Uncontrolled Keywords: cycloaddition; photochemistry; butadienes; benzobicyclo[3.2.1.]octadiene; polycyles
Subjects: NATURAL SCIENCES > Chemistry
Divisions: NMR Center
Projects:
Project titleProject leaderProject codeProject type
Spektroskopija NMR i modeliranje bioaktivnih molekula[76010] Dejan Plavšić098-0982929-2917MZOS
Heteropolicikli, strukturne osnove za bioaktivne spojeve. Sinteza i fotokemija[235422] Irena Škorić125-0982933-2926MZOS
Depositing User: Sofija Konjević
Date Deposited: 10 Mar 2015 14:41
Last Modified: 17 Mar 2015 11:09
URI: http://fulir.irb.hr/id/eprint/1715
DOI: 10.5562/cca2454

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