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The reaction of ferrocenyldiphenylphosphine with styrene oxide in ethanol gives, as the major product, ferrocenyl(phenyl)(1,2-diphenylethyl)phosphine oxide (5, R = Ph), the result of a rearrangement involving phenyl migration from phosphorus to adjacent carbon in the decomposition of a vinylphosphonium ion arising from protonation and subsequent elimination of water from the initially-formed phosphonium betaine. A related phenyl migration occurs in the reaction of the phosphine with ethyl propiolate in wet THF. The presence of a ferrocenyl group at phosphorus in Wittig reactions of semistabilised ylides causes the expected decrease in the cis-trans ratio of the resulting alkenes, consistent with its behaviour as an electron-donating substituent.

zeitschrift für naturforschung b

Reactions of Ferrocenyldiphenylphosphine. Effects of the Ferrocenyl Group at Phosphorus on the Course of Decomposition of Phosphonium Betaines and Vinylphosphonium Salts