Croatica Chemica Acta, Vol. 87 No. 4, 2014.
Original scientific paper
https://doi.org/10.5562/cca2454
Photochemical Approach to New Polycyclic Substrates Suitable for Further Photocatalytic Functionalization
Dragana Vuk
; Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 19, 10000 Zagreb, Croatia
Željko Marinić
orcid.org/0000-0002-7459-1451
; Center for NMR, Rudjer Bošković Institute, Bijenička cesta 54, 10000 Zagreb, Croatia
Irena Škorić
orcid.org/0000-0002-1563-7261
; Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 19, 10000 Zagreb, Croatia
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 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
cycloaddition; photochemistry; butadienes; benzobicyclo[3.2.1.]octadiene; polycycles
Hrčak ID:
131548
URI
Publication date:
22.12.2014.
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