Photochemical Approach to New Polycyclic Substrates Suitable for Further Photocatalytic Functionalization

Scientific paper - Original scientific paper

• Author: Dragana Vuk
• Author: Željko Marinić; MBZ: 115246
• Author: Irena Škorić
• Author's institution: Ruđer Bošković Institute
• Author's institution: University of Zagreb; Faculty of Chemical Engineering and Technology; (Deprtment of Organic Chemistry)
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract (english)

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 benzobicy-clo[3.2.1]octadienes endo,endo-19 and endo,endo-20 are formed, respectively. New bicy-clo[3.2.1]octadienes with isolated double bond can be suitable substrates for further efficient photo-catalytic oxygenations in course of new functionalized polycycles, potentially new biologically active compounds.

• Keywords (english): cycloaddition; photochemistry; butadienes; benzobicyclo[3.2.1.]octadiene; polycycles
• Language: english
• Publication type: Scientific paper - Original scientific paper
• Publication status: Published
• Peer review: Peer review
• Publication version: Published version
• Journal title: Croatica chemica acta
• Numbering: vol. 87, no. 4, pp. 465-473
• p-ISSN: 0011-1643
• e-ISSN: 1334-417X
• DOI: https://doi.org/10.5562/cca2454
• URN:NBN: urn:nbn:hr:149:849919
• Publication: 2014-12-22
• Project: Number: 125-0982933-2926; Title (croatian): Heteropolicikli, strukturne osnove za bioaktivne spojeve. Sinteza i fotokemija; Leader: Irena Škorić; Jurisdiction: Croatia
• Project: Number: 098-0982929-2917; Title (croatian): Spektroskopija NMR i modeliranje bioaktivnih molekula; Leader: Dejan Plavšić; Jurisdiction: Croatia
• Document URL: http://hrcak.srce.hr/131548
• Type of resource: Text
• Access conditions: Open access
• Repository: Repository of Faculty of Chemical Engineering and Technology University of Zagreb
• Created on: 2017-03-08 12:59:57