SPANphos

Names

IUPAC name
4,4,4′,4′,6,6′-Hexamethyl-2,2′-spirobichroman-8,8′-diylbis(diphenylphosphane)

Properties

Chemical formula

C47H46O2P2

Molar mass
704.814 g/mol

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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Infobox references

SPANphos is an organophosphorus compound used as a ligand in organometallic and coordination chemistry. This compound is a rare example of a trans-spanning ligand and rigidly links mutually trans coordination sites. By virtue of its chiral backbone that forms a chiral cavity over the face of a square planar complexes, e.g. in MCl2(SPANphos) (M = Pd, Pt).
Synthesis[edit]
This C2-symmetric trans-diphosphine is synthesized from inexpensive reagents. In the first step 4,4,4′,4′,6,6′-hexamethyl-2,2′-spirobichroman is prepared via an acid-catalyzed reaction between p-cresol and acetone. The spirane is brominated with N-bromosuccinimide, and the resulting dibromide is metalated with n-BuLi. Treatment of the resulting dilithio derivative with chlorodiphenylphosphine completes the synthesis.[1]

References[edit]

^ Z. Freixa, M. S. Beentjes, G. D. Batema, C. B. Dieleman, G. P. F. v. Strijdonck, J. N. H. Reek, P. C. J. Kamer, J. Fraanje, K. Goubitz and P. W. N. M. Van Leeuwen (2003). “SPANphos: A C2-Symmetric trans-Coordinating Diphosphane Ligand”. Angewandte Chemie. 42 (11): 1322–1325. doi:10.1002/anie.200390330. PMID 12645065.  CS1 maint: Multiple names: authors list (link)

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