Approaches to water-soluble phosphines. II. Free radical addition reactions of phenylphosphines
Free radical additions of diphenylphosphine, phenylphosphine and ethylenebis(phenylphosphine) to the following species are described: alkynols, alkyne ethers, unsaturated carboxylic acids and esters and β-lactones.In a number of cases, these lead to water-soluble phosphines.NMR spectroscopic characterization of all new products has been carried out.Key words: Phosphine; Water soluble phosphines; Radical addition; Chirality
Heesche-Wagner, Kerstin,Mitchell, Terence N.
p. 99 - 106
(2007/10/02)
ADDITION OF DIPHENYLPHOSPHINE TO MALEIC ANHYDRIDE AND RELATED COMPOUNDS
A Michael addition of secondary phosphines to activated olefins containing the ethenedione moiety such as maleic anhydride, maleic ester and dibenzoylethene leads to functionalised tertiary phosphines.Reactions of activated olefins which contain a carboxylic group do not lead to the expected products; instead, phosphonium salts are formed by a sequence of reactions.A hydrogen shift plays a crucial role both in the reaction that leads to the adduct and in the reaction that leads to the phosphonium salt.Phosphinosuccinic anhydrides and phosphinosuccinic esters can betransformed into the corresponding succinic acids.Decarboxylation of phosphinosuccinic acids leads to phosphinopropionic acids.
Doorn, J. A. van,Wife, R. L.
p. 253 - 260
(2007/10/02)
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