Key indicatorsSingle-crystal X-ray study T = 173 K Mean (C-C) = 0.002 Å R factor = 0.034 wR factor = 0.085 Data-to-parameter ratio = 18.0 For details of how these key indicators were automatically derived from the article, see

Allylic phosphonium ylides are readily generated by the combination of an allylic alcohol, a carbene, and a chlorophosphite. Here we demonstrate that these intermediates undergo a thermal [3,3]-rearrangement to provide single isomers of homoallylic phosphonates in good to excellent yields. This new reaction manifold for phosphorus ylides is tolerant of a range of substitution patterns on the reactants and provides access to structurally complex intermediates for the synthesis of enzyme inhibitors, aminophosphonic acids, and natural products.

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Organo-phosphorus compounds S 0080 [3,3]-Rearrangements of Phosphonium Ylides. -The reaction of an allylic alcohol, a chlorophosphite like compound (I), and a carbene derived from a diazo compound affords allylic phosphonium ylides. These intermediates undergo a thermal [3,3] rearrangement to give single isomers of homoallylic phosphonates in good to excellent yields. -(FERGUSON, M. L.; SENECAL, T. D.; GROENDYKE, T. M.; MAPP*, A. K.; J.