SPANphos

Quality 0.50 · 0 views · Updated 2 months ago

title: "SPANphos" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["diphosphines", "benzopyrans", "spiro-compounds"] topic_path: "general/diphosphines" source: "https://en.wikipedia.org/wiki/SPANphos" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| verifiedrevid = 409102763 | ImageFile = SPANphos.svg | PIN = (4,4,4′,4′,6,6′-Hexamethyl-3,3′,4,4′-tetrahydro-2,2′-spirobi[[1]benzopyran]-8,8′-diyl)bis(diphenylphosphane) |Section1 = {{Chembox Identifiers | CASNo = 556797-94-5 | CASNo_Ref = | ChemSpiderID = 57592633 | EC_number = 814-334-7 | PubChem = 12103420 | 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 | InChIKey = RQMTZMWXNZQOPD-UHFFFAOYSA-N | 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 |Section2 = {{Chembox Properties | Formula = C47H46O2P2 | MolarMass = 704.814 g/mol

SPANphos is an organophosphorus compound used as a ligand in organometallic and coordination chemistry. The 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).[[File:WABXIH.png|thumb|left|144px|Structure of PtCl2(SPANphos)]]

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. :[[File:SPANphosPrep.png|thumb|center|344px|Preparation of SPANphos from p-[[cresol]]]]

References

References

  1. Z. Freixa, M. S. Beentjes, G. D. Batema, C. B. Dieleman, G. P. F. van Strijdonck, J. N. H. Reek, P. C. J. Kamer, J. Fraanje, K. Goubitz and P. W. N. M. van Leeuwen. (2003). "SPANphos: A ''C''2-Symmetric ''trans''-Coordinating Diphosphane Ligand". Angewandte Chemie International Edition.

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::

diphosphinesbenzopyransspiro-compounds