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The stereochemical course of the ‘phosphine oxide cleavage’ of chiral R-(+)-methylphenyl-α-naphthyl-allyl-phosphonium bromide is reported. While the α-naphthyl group is cleaved by alkali with predominant retention of configuration at the central phosphorus atom, the allyl group is split off with predominant inversion.

zeitschrift für naturforschung b

Zur Stereochemie der Phosphinoxydspaltung von R-(+)-Methyl-phenyl-α -naphthyl-allyl-phosphoniumbromid / The Stereochemistry of the Phosphine Oxide Cleavage of R-(+)-Methyl-phenyl-α-naphthyl-allyl-phosphonium Bromide