Photocycloadditionen captodativer Olefine an Indole, Benzo[b]thiophene und -furane - Photocycloadditions capto-dative alkenes to Indoles, benzo[b]thiophenes and -furanes
In examine the photocycloadditions of the title compounds the following questions are of interest: 1. Aside of [2+2]-cycloadditions to the C(2)=C(3) bonds, can any cycloaddition occur to the benzoid ring? 2. Which factors govern the regio- and stereoselectivity? Irradiation of either benzo[b]pyrrole-, -furane- or -thiophene-2-carboxylates in the presence of 2-morpholinopropennitril in cyclohexane leads, in a highly regioselective reaction, to [2+2] photoadducts. The regioselectivity seems to follow the formation of the most stable intermediate 1,4-biradicals. No photocycloadditions of the title alkene have been observed with 4-acceptor substituted benzo[b]pyrroles.
Advisor:Prof. Dr. Wolfgang Gärtner; Prof. Dr. Dietrich Döpp
School:Universität Duisburg-Essen, Standort Essen
Source Type:Master's Thesis
Keywords:chemie gerhard mercator universitaet
Date of Publication:12/10/2002