Abstract
THE unique ability of dipolar solvents to promote carbanion reactions has been the subject of two recent reviews1,2. More specifically, the use of a dimethyl-sulphoxide (80 per cent)-tert-butyl alcohol mixture as a medium for the autoxidation of carbanions3,4 and N,N-dialkyl amides as media for the autoxidation of mercaptide ions5–7 has been demonstrated. Zaugg8 has shown that pyridine-N-oxide (PNO) is capable of accelerating the alkylation of enolate anions and other carbanions by alkyl halides in inert solvents. In the present communication, we report the results of our investigations in which we have attempted to use compounds containing an N–O linkage as solvents for base-catalysed oxidation reactions.
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For a discussion see refs. 3 and 4.
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WALLACE, T., HOFMANN, J. & POBINER, H. Autoxidation of Carbanions in Azoxybenzene. Nature 204, 376–377 (1964). https://doi.org/10.1038/204376a0
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DOI: https://doi.org/10.1038/204376a0
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