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Mechanism of Phosphorus-Carbon Bond Cleavage by Lithium in Tertiary Phosphines. An Optimized Synthesis of 1,2-Bis(phenylphosphino)ethane

Dogan, John; Schulte, Jurgen; Swiegers, Gerhard; Wild, Stanley (Bruce)


Conditions influencing the extent of P-C(aryl) vs P-C(alkyl) bond cleavage in the reaction of Ph2P(CH2)2PPh2 with lithium in THF have been investigated. The results complement and elucidate earlier work; they indicate that the mechanism of P-C bond cleavage in tertiary phosphines of this type involves a thermodynamic equilibrium between P-C(aryl) and P- C(alkyl) cleaved radicals and anions, followed by reaction and stabilization of these as lithium salts. The addition of water to the reaction...[Show more]

CollectionsANU Research Publications
Date published: 2000
Type: Journal article
Source: Journal of Organic Chemistry
DOI: 10.1021/jo9907336


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