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Issue 16, 1983
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A new route to chiral bis-tertiary phosphine ligands: synthesis, resolution, and crystal structure of trans-bis-1,2-(diphenylphosphino)-cyclopentane and the nickel adduct NiBr2[trans-1,2-(PPh2)2C5H8]

Abstract

Heating of white phosphorus, phosphorus trichloride, and cyclopentene at 220 °C gives trans-1,2-bis (dichlorophosphino)cyclopentane (1), which with phenylmagnesium bromide gives trans-1,2-bis(diphenylphosphino)-cyclopentane (dpcp)(2); compound (2)forms the adduct Ni(dpcp) Br2·CH2Cl2, which readily crystallizes as a conglomerate and the pure enantiomers may be separated by hand allowing resolution of (2), and catalytic hydrogenation of methyl(N-benzoyl) dehydrophenylalanine using resolved (2)and a rhodium catalyst gave a hydrogenated product of 100% optical purity.

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Article information


J. Chem. Soc., Chem. Commun., 1983, 895-896
Article type
Paper

A new route to chiral bis-tertiary phosphine ligands: synthesis, resolution, and crystal structure of trans-bis-1,2-(diphenylphosphino)-cyclopentane and the nickel adduct NiBr2[trans-1,2-(PPh2)2C5H8]

D. L. Allen, V. C. Gibson, M. L. H. Green, J. F. Skinner, J. Bashkin and P. D. Grebenik, J. Chem. Soc., Chem. Commun., 1983, 895
DOI: 10.1039/C39830000895

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