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A Synthetic Route to a New Surface-Active Phosphine Ligand: 12-DPDP (12-Diphenylphosphinododecylphosphonate)

✍ Scribed by Terence L Schull; L Renée Olano; D Andrew Knight

Book ID
104202859
Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
88 KB
Volume
56
Category
Article
ISSN
0040-4020

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✦ Synopsis

A water-soluble phosphonate-functionalized phosphine ligand Na 2 [Ph 2 P(CH 2 ) 12 PO 3 ] (8), was prepared in eight steps from cyclododecanone. Phosphine 8 reacts with [Rh(COD)Cl] 2 in methanol to give the new complex Na 2 [Rh(COD)(Ph 2 P(CH 2 ) 12 PO 3 )Cl] (9). Complex 9 is inactive in the catalytic hydrogenation of 1-hexene and cyclohexene due to the decomposition of 9 to rhodium metal in the presence of hydrogen gas. Hydrogenation of decene using [Rh(COD) 2 ]BF 4 and 3 equiv. of 8 in an aqueous emulsion was achieved using 1 atm H 2 . 31 P NMR studies on 8 suggest a lack of well-defined aggregation in water, which has been ascribed to the steric bulk of the diphenylphosphino group.

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