Original scientific paper

Photochemistry of p-(5-Substituted-2-furyl)-o-divinylbenzenes; Substituent Effects on the Reaction Course

Marija Šindler-Kulyk ; Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 19, 10000 Zagreb, Croatia
Goran Kragol ; Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 19, 10000 Zagreb, Croatia
Ivo Piantanida ; Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 19, 10000 Zagreb, Croatia
Slavica Tomšić ; Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 19, 10000 Zagreb, Croatia
Irena Vujković Cvijin ; Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 19, 10000 Zagreb, Croatia
Željko Marinić ; Ruđer Bošković Institute, P.O.B. 1016, HR-10001 Zagreb, Croatia
Biserka Metelko ; Ruđer Bošković Institute, P.O.B. 1016, HR-10001 Zagreb, Croatia

Abstract

Irradiation of 2-[2-(2-vinylphenyl)ethenyl]furan (la) and 5-methyl- 2-[2-(2-vinylphenyl)ethenyl]furan (lb) gave 9,10-đihydro-4,9-me- thano-4ff-benzo[4,5]cyclohepta[l,2-6]furan (2a) and 9,10-dihydro- 2-methyl-4,9-methano-4H-benzo[4,5]cyclohepta[l,2-b]furan (2b), respectively, in a very good yield in addition to traces of 5. Contrary to these results, the 5-substituted furan derivatives 1 (c: R = CN; d: R = P-C6H4CH3, e: R = OCH3) gave mainly, upon irradiation under the same conditions, isomerization about the double bond, high-molecular-weight products, small amount of phenanthrenes 5 and only traces of bicyclic structure 2.

Keywords

Hrčak ID:

135993

URI

https://hrcak.srce.hr/135993

Publication date:

2.12.1996.

Visits: 1.430 *