SPANphos

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SPANphos
SPANphos.svg
Names
Preferred IUPAC name
(4,4,4′,4′,6,6′-Hexamethyl-3,3′,4,4′-tetrahydro-2,2′-spirobi[[1]benzopyran]-8,8′-diyl)bis(diphenylphosphane)
Identifiers
3D model (JSmol)
PubChem CID
  • 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
  • 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
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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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).

Structure of PtCl2(SPANphos) WABXIH.png
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. [1]

Preparation of SPANphos from p-cresol SPANphosPrep.png
Preparation of SPANphos from p-cresol

Related Research Articles

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<i>Cis</i>–<i>trans</i> isomerism Pairs of molecules with same chemical formula showing different spatial orientations

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<span class="mw-page-title-main">Inorganic chemistry</span> Field of chemistry

Inorganic chemistry deals with synthesis and behavior of inorganic and organometallic compounds. This field covers chemical compounds that are not carbon-based, which are the subjects of organic chemistry. The distinction between the two disciplines is far from absolute, as there is much overlap in the subdiscipline of organometallic chemistry. It has applications in every aspect of the chemical industry, including catalysis, materials science, pigments, surfactants, coatings, medications, fuels, and agriculture.

<span class="mw-page-title-main">Manganese(II) chloride</span> Chemical compound

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<span class="mw-page-title-main">Cobalt(II) chloride</span> Chemical compound

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2
. The compound forms several hydrates CoCl
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·nH
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O
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<span class="mw-page-title-main">Octahedral molecular geometry</span> Molecular geometry

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<span class="mw-page-title-main">1,4,7-Triazacyclononane</span> Chemical compound

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<span class="mw-page-title-main">Gold(III) bromide</span> Chemical compound

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<span class="mw-page-title-main">Chloro(dimethyl sulfide)gold(I)</span> Chemical compound

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References

  1. 1 2 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 C2-Symmetric trans-Coordinating Diphosphane Ligand". Angewandte Chemie International Edition. 42 (11): 1322–1325. doi:10.1002/anie.200390330. PMID   12645065.{{cite journal}}: CS1 maint: multiple names: authors list (link)