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{{chembox |
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{{chembox |
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| verifiedrevid = 409102763 |
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| IUPACName = 4,4,4',4',6,6'-Hexamethyl-2,2'-spirobichroman-8,8'-diylbis(diphenylphosphane) |
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| ImageFile = SPANphos.png |
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| ImageFile = SPANphos.svg |
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| PIN = (4,4,4′,4′,6,6′-Hexamethyl-3,3′,4,4′-tetrahydro-2,2′-spirobibenzopyran]-8,8′-diyl)bis(diphenylphosphane) |
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| Section1 = {{Chembox Properties |
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|Section1 = {{Chembox Identifiers |
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| Formula = C<sub>47</sub>H<sub>46</sub>O<sub>2</sub>P<sub>2</sub> |
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| CASNo = 556797-94-5 |
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| MolarMass = 704.814 g/mol |
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| CASNo_Ref = {{Cascite|changed|}} |
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| PubChem = 12103420 |
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| 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 |
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| InChIKey = RQMTZMWXNZQOPD-UHFFFAOYSA-N |
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| 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 |
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|Section2 = {{Chembox Properties |
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| Formula = C<sub>47</sub>H<sub>46</sub>O<sub>2</sub>P<sub>2</sub> |
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| MolarMass = 704.814 g/mol |
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'''SPANphos''' is an ] used as a ligand in ] and ]. This compound is a rare example of a ] 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 MCl<sub>2</sub>(SPANphos) (M = Pd, Pt). |
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'''SPANphos''' is an ] used as a ligand in ] and ]. The compound is a rare example of a ] and rigidly links mutually trans coordination sites. By virtue of its C<sub>2</sub>-symmetric backbone, SPANphos forms a chiral cavity over the face of a square planar complexes, e.g. in MCl<sub>2</sub>(SPANphos) (M = Pd, Pt).] |
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==Synthesis== |
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==Synthesis== |
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This C<sub>2</sub>-symmetric trans-] 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 ] and ]. The spirane is brominated with ], and the resulting dibromide is metalated with ]. Treatment of the resulting dilithio derivative with ] completes the synthesis.<ref>{{cite journal | author = 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 | title = SPANphos: A ''C''<SUB><FONT SIZE='-1'>2</FONT></SUB>-Symmetric ''trans''-Coordinating Diphosphane Ligand | journal = ] | year = 2003 | volume = 42 | issue = 11 | pages = 1322–1325 |doi = 10.1002/anie.200390330 | pmid = 12645065 }}</ref> |
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SPANphos can be prepared synthesized from relatively inexpensive reagents. In the first step 4,4,4',4',6,6'-hexamethyl-2,2'-spirobi] is prepared via an acid-catalyzed reaction of ] and ]. The resultant spirocycle is halogenated with ] followed by lithium-bromide exchange using ]. Treatment of the resulting ] compound with ] completes the synthesis.<ref name=Freixa>{{cite journal | author = 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 | title = SPANphos: A ''C''<SUB>2</SUB>-Symmetric ''trans''-Coordinating Diphosphane Ligand | journal = Angewandte Chemie International Edition | year = 2003 | volume = 42 | issue = 11 | pages = 1322–1325 |doi = 10.1002/anie.200390330 | pmid = 12645065}}</ref> |
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==References== |
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==References== |
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