Photocycloadditions capto-dative alkenes to Indoles, benzo[b]thiophenes and -furanes

Derivate 5406

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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.
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Dokumententyp:
Wissenschaftliche Abschlussarbeiten » Dissertation
Fakultät / Institut:
Fakultät für Chemie
Dewey Dezimal-Klassifikation:
500 Naturwissenschaften und Mathematik » 540 Chemie
Keywords:
syn, dative, UV-spectrum, irradiation, photoaddition, thermolyses, analytical devices, donor, addition, photocycloadducts, regiocontrol, diradical, photo-fries-rearrangement, benzo[b]pyrrole, cycloadditions, concerted, photoexcited, electronic excited, addition, quenching of fluorescence, single crystal X-ray structural analysis, photoreactions, radicophile, dimerisation, stereocontrol
Contributors:
Prof. Dr. Döpp, Dietrich [Thesis advisor]
Prof. Dr. Gärtner, Wolfgang [Reviewer]
Language:
Deutsch
Collection / Status:
Dissertations / Document published
Date of doctoral degree:
09.10.2002
Document created on:
09.10.2002
Files changed on:
13.10.2006
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Text