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Synthesis, structure and pyrolysis of stabilised phosphonium ylides containing saturated oxygen heterocycles
Aitken, R.A. Karodia, Nazira McCarron, H.B. Rouxel, C. Sahabo, Nina Carole Slawin, A.M.Z.
Aitken, R.A.
Karodia, Nazira
McCarron, H.B.
Rouxel, C.
Sahabo, Nina Carole
Slawin, A.M.Z.
Publication Date
2016-04
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© 2016 The Royal Society of Chemistry. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
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2016-01-05
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Abstract
A range of twelve stabilised phosphonium ylides containing tetrahydrofuran, tetrahydropyran or 2,2-
dimethyl-1,3-dioxolane rings have been prepared and fully characterised, including one X-ray structure
determination of each type. The X-ray structures confirm the PvC and CvO functions to be syn and all
the compounds undergo thermal extrusion of Ph3PO to give the corresponding alkynes. In some cases
there is also competing loss of Ph3P to give different carbene-derived products and evidence has been
obtained for the generation of 2-phenyloxete in this way. Raising the pyrolysis temperature leads in
several cases to new secondary reactions of the alkyne products involving a sequence of alkyne to vinylidene
isomerisation, intramolecular CH insertion, and retro Diels Alder reaction.
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Aitken RA, Karodia N, McCarron HB, Rouxel C, Sahabo N and Slawina AMZ (2016) Synthesis, structure and pyrolysis of stabilised phosphonium ylides containing saturated oxygen heterocycles. Organic & Biomolecular Chemistry. 14: 1794-1804.
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