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SPANphos
Sign in to saveSPANphos 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).thumb|left|144px|Structure of PtCl2(SPANphos)
Chemical data
- Formula
- C47H46O2P2
- Molecular weight
- 704.8 g/mol
- IUPAC name
- (8'-diphenylphosphanyl-4,4,4',4',6,6'-hexamethyl-2,2'-spirobi[3H-chromene]-8-yl)-diphenylphosphane
- SMILES
- CC1=CC2=C(C(=C1)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5(CC2(C)C)CC(C6=C(O5)C(=CC(=C6)C)P(C7=CC=CC=C7)C8=CC=CC=C8)(C)C
- InChIKey
- RQMTZMWXNZQOPD-UHFFFAOYSA-N
- XLogP
- 12.2
- Polar surface area
- 18.5 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Has part
- hydrogen
- Mass
- 704.297303972
Show 2 more facts
- chemical formula
- C₄₇H₄₆O₂P₂
- canonical SMILES
- CC1=CC2=C(C(=C1)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5(CC2(C)C)CC(C6=C(O5)C(=CC(=C6)C)P(C7=CC=CC=C7)C8=CC=CC=C8)(C)C
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Encyclopedic overview
2 sectionsContents
- Synthesis
- References
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).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. thumb|center|344px|Preparation of SPANphos from p-cresol
Excerpted from Wikipedia’s “SPANphos” article, available under the CC BY-SA 4.0 licence.