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Oxygen transfer reaction from cyclic nitrones to triphenylphosphine

University of British Columbia

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.

Text

2011-11-08

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http://hdl.handle.net/2429/38874

Chemistry

University of British Columbia

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