Reactions of photoexcited 1,2-dicarbonyl compounds with chirally labelled and unlabelled captodative alkenes have been investigated, with special emphasis on their diastereoselection in cycloadditions. Irradiation of methyl phenylglyoxylate in presence of unlabelled alkenes yields to the corresponding rel-(2R, 3R)-head-to-head-oxetanes. Using the chirally labelled (S)-(methoxymethylpiperidinyl)propenenitrile gives rise to two oxetanes, one of which was isolated and identified as (2R, 3R)-head-to-head-oxetane by X-ray cristallography. Additionally, the photoreduction product meso-dimethyl-2,3-diphenyltartrate of the ester was formed in all reactions. The photoreactions of benziles with chirally labelled c,d-alkenes give rise to oxetanes in low yields, in these cases the products of Norrish type I reactions become competitive.
| Identifer | oai:union.ndltd.org:DUETT/oai:DUETT:duett-05132002-111352 |
| Date | 29 May 2002 |
| Creators | Wolven, Christiane van |
| Contributors | Prof. Dr. D. Döpp, Prof. Dr. M. Tausch |
| Publisher | Gerhard-Mercator-Universitaet Duisburg |
| Source Sets | Dissertations and other Documents of the Gerhard-Mercator-University Duisburg |
| Language | German |
| Detected Language | English |
| Type | text |
| Format | text/html, application/pdf |
| Source | http://www.ub.uni-duisburg.de/ETD-db/theses/available/duett-05132002-111352/ |
| Rights | unrestricted, I hereby certify that, if appropriate, I have obtained and attached hereto a written permission statement from the owner(s) of each third party copyrighted matter to be included in my thesis, dissertation, or project report, allowing distribution as specified below. I certify that the version I submitted is the same as that approved by my advisory committee. Hiermit erteile ich der Universitaet Duisburg das nicht-ausschliessliche Recht unter den unten angegebenen Bedingungen, meine Dissertation, Staatsexamens- oder Diplomarbeit, meinen Forschungs- oder Projektbericht zu veroeffentlichen und zu archivieren. Ich behalte das Urheberrecht und das Recht das Dokument zu veroeffentlichen und in anderen Arbeiten weiterzuverwenden. |
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