Abstract

Two α-phenylselenophosphoranes (III R-H or Me) were allowed to react with cyclohexanone giving instead of the expected olefinic Wittig product the corresponding 2-phenylselenocyclohexanone (VI). The reaction pathuay has been demonstrated to involve nucleophilic substitution on selenium by the katone enolate, the leaving group being the selenium free phosphorane (I). This reaction is shown to be general for seven more ketones, thus indicating its preparative potential.

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