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 title	Project leader	Project code	Project type
Spektroskopija NMR i modeliranje bioaktivnih molekula	[76010] Dejan Plavšić	098-0982929-2917	MZOS
Heteropolicikli, strukturne osnove za bioaktivne spojeve. Sinteza i fotokemija	[235422] Irena Škorić	125-0982933-2926	MZOS

Depositing User:

Sofija Konjević

Date Deposited:

10 Mar 2015 14:41

URI:

http://fulir.irb.hr/id/eprint/1715

DOI:

10.5562/cca2454