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The ylidyl substituent of the chlorophosphane Ph3P(DOUBLE BOND)CAr(SINGLE BOND)PRCl exerts a strong influence on the P(SINGLE BOND)Cl bond. An X‐ray structure investigation of the representative with Ar(DOUBLE BOND)Ph, R(DOUBLE BOND)Me reveals the longest P(SINGLE BOND)Cl bond ever observed for an acyclic chlorophosphine (226.2(1) pm). It is connected to a conformation that allows an effective negative hyperconjugation. The ylidyl chlorophosphanes with an amino group R are covalent in benzene but become more or less ionic in dichloromethane solution. The solvent‐dependent dissociation equilibrium can be followed by 31P NMR spectra. In case of an enamine‐derived ylidyl chlorophosphane, the equilibrium shifts almost completely from the covalent to the ionic side within a rather narrow range of solvent composition (20 to 70 vol % dichloromethane). © 1996 John Wiley & Sons, Inc.
Heteroatom Chemistry – Wiley
Published: Jan 1, 1996
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