SPANphos

SPANphos
Names
	IUPAC name 4,4,4',4',6,6'-Hexamethyl-2,2'-spirobichroman-8,8'-diylbis(diphenylphosphane)
Identifiers
3D model (JSmol)	Interactive image;
PubChem CID	12103420;
	InChI InChI=1S/C47H46O2P2/c1-33-27-39-43(41(29-33)50(35-19-11-7-12-20-35)36-21-13-8-14-22-36)48-47(31-45(39,3)4)32-46(5,6)40-28-34(2)30-42(44(40)49-47)51(37-23-15-9-16-24-37)38-25-17-10-18-26-38/h7-30H,31-32H2,1-6H3 Key: RQMTZMWXNZQOPD-UHFFFAOYSA-N;
	SMILES CC1=CC(=C2C(=C1)C(CC3(O2)CC(C4=CC(=CC(=C4O3)P(C5=CC=CC=C5)C6=CC=CC=C6)C)(C)C)(C)C)P(C7=CC=CC=C7)C8=CC=CC=C8;
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 C₂-symmetric backbone, SPANphos forms a chiral cavity over the face of a square planar complexes, e.g. in MCl₂(SPANphos) (M = Pd, Pt).

Structure of PtCl₂(SPANphos)[1]

Synthesis

SPANphos can be prepared synthesized from relatively inexpensive reagents. In the first step 4,4,4',4',6,6'-hexamethyl-2,2'-spirobichromane is prepared via an acid-catalyzed reaction of p-cresol and acetone. The resultant spirocycle is halogenated with N-bromosuccinimide followed by lithium-bromide exchange using n-BuLi. Treatment of the resulting dilithio compound with chlorodiphenylphosphine completes the synthesis.[1]

Preparation of SPANphos from p-cresol

References

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 International Edition. 42 (11): 1322–1325. doi:10.1002/anie.200390330. PMID 12645065.CS1 maint: multiple names: authors list (link)

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[Freixa-1] 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 International Edition. 42 (11): 1322–1325. doi:10.1002/anie.200390330. PMID 12645065.CS1 maint: multiple names: authors list (link)