Pyrolysis of Stabilised Phosphorus Ylides as a Route to new Hetero Carbenes

R. Alan Aitken Department of Chemistry, University of St. Andrews, North Haugh, St. Andrews, Fife, KY16 9ST, UK

Martin J. Drysdale Department of Chemistry, University of St. Andrews, North Haugh, St. Andrews, Fife, KY16 9ST, UK

Adrian Ford Department of Chemistry, University of St. Andrews, North Haugh, St. Andrews, Fife, KY16 9ST, UK

Paul E. Y. Milne Department of Chemistry, University of St. Andrews, North Haugh, St. Andrews, Fife, KY16 9ST, UK

Duncan W. Russell Department of Chemistry, University of St. Andrews, North Haugh, St. Andrews, Fife, KY16 9ST, UK

Bruce M. Ryan Department of Chemistry, University of St. Andrews, North Haugh, St. Andrews, Fife, KY16 9ST, UK

Martin Whittaker Department of Chemistry, University of St. Andrews, North Haugh, St. Andrews, Fife, KY16 9ST, UK

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Abstract

Flash vacuum pyrolysis of sulphonyl- and sulphinyl-stabilised phosphorus ylides results in loss of either phosphine or phosphine oxide to generate thio-, sulphinyl- and sulphonyl-carbenes which undergo a variety of rearrangement and insertion processes to give stable products. The first case of phosphine extrusion from a ß-oxo ylide is reported, giving access to benzotriazolyl acetyl carbene which rearranges to an acetyl benzotriazine and 2-cyanoacetophenone.

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Pyrolysis of Stabilised Phosphorus Ylides as a Route to new Hetero Carbenes

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Pyrolysis of Stabilised Phosphorus Ylides as a Route to new Hetero Carbenes

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