The compounds in the series from triphenylphosphine to triphenylbismuthine were examined as acceptors in oxygen transfer reactions involving the l-pyrroline-l-oxides. Triphenylphosphine was found to offer a useful route from the l-pyrroline-l-oxides to the corresponding pyrrolines.
The second part of this work is centred on the structural investigation of Sanno's base (XV) (l), obtained as a by-product in the reductive cyclization of ethyl
2-acetyl-2-ethyl-4-methyl-3-nitromethyl valerate (aγ -nitro-ketone) and formulated by the author as having the Δ’ -pyrroline structure; this compound has since been found to be a cyclic nitrone (XVI). In the case of this complex nitrone, the oxygen transfer reaction to triphenylphosphine has been successful, yielding two isomeric Δ' -pyrrolines.
The isolation of a Δ -pyrroline structure is confirmation of the proposed cyclic nitrone (XVI) structure for Sanno's base and as this provides a practical application of this reaction in structural work as well as showing that triphenylphosphine will reduce N-oxides in the presence of an ester group. / Science, Faculty of / Chemistry, Department of / Graduate
| Identifer | oai:union.ndltd.org:UBC/oai:circle.library.ubc.ca:2429/38874 |
| Date | January 1962 |
| Creators | Agolini, Franco |
| Publisher | University of British Columbia |
| Source Sets | University of British Columbia |
| Language | English |
| Detected Language | English |
| Type | Text, Thesis/Dissertation |
| Rights | For non-commercial purposes only, such as research, private study and education. Additional conditions apply, see Terms of Use https://open.library.ubc.ca/terms_of_use. |
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