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The observation of unusually stable oxaphosphetanes derived from one semistabilized[5] and one stabilized ylide[8] has recently been reported. In the semistabilized case, a dibenzophosphole substituted phosphorus atom in the oxaphosphetane is stabilized relative to the phosphine oxide product, hence the decomposition rate is retarded. In the stabilized case, resistance to oxaphosphetane decomposition is provided by the stabilizing effects of electron-withdrawing groups and ring strain on the phosphorus atom.
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