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Oxygen transfer reaction from cyclic nitrones to triphenylphosphine Agolini, Franco

Abstract

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.

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