SPANphos: Difference between revisions
Content deleted Content added
m H |
spelling of authors |
||
| (25 intermediate revisions by 19 users not shown) | |||
| Line 1: | Line 1: | ||
{{chembox |
{{chembox |
||
| verifiedrevid = 409102763 |
|||
| IUPACName = 4,4,4',4',6,6'-Hexamethyl-2,2'-spirobichroman-8,8'-diylbis(diphenylphosphane) |
|||
| |
| ImageFile = SPANphos.svg |
||
| PIN = (4,4,4′,4′,6,6′-Hexamethyl-3,3′,4,4′-tetrahydro-2,2′-spirobi[<nowiki/>[1]benzopyran]-8,8′-diyl)bis(diphenylphosphane) |
|||
| ⚫ | |||
|Section1 = {{Chembox Identifiers |
|||
| ⚫ | |||
| CASNo = 556797-94-5 |
|||
| ⚫ | |||
| CASNo_Ref = {{Cascite|changed|}} |
|||
| ⚫ | |||
| 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 |
|||
| ⚫ | |||
| ⚫ | |||
| ⚫ | |||
| ⚫ | |||
}} |
|||
}} |
}} |
||
'''SPANphos''' is an [[organophosphorus compound]] used as a ligand in [[organometallic chemistry|organometallic]] and [[coordination chemistry]]. |
'''SPANphos''' is an [[organophosphorus compound]] used as a ligand in [[organometallic chemistry|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 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).[[File:WABXIH.png|thumb|left|144px|Structure of PtCl<sub>2</sub>(SPANphos)<ref name=Freixa/>]] |
||
==Synthesis== |
==Synthesis== |
||
SPANphos can be prepared synthesized from relatively inexpensive reagents. In the first step 4,4,4',4',6,6'-hexamethyl-2,2'-spirobi[[chromane]] 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 [[butyl lithium|n-BuLi]]. Treatment of the resulting [[organolithium|dilithio]] compound with [[chlorodiphenylphosphine]] 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> |
|||
:[[File:SPANphosPrep.png|thumb|center|344px|Preparation of SPANphos from p-[[cresol]]]] |
|||
:[[Image:Synthesis of SPANphos.png|500px]] |
|||
==References== |
==References== |
||
<references/> |
<references/> |
||
[[Category: |
[[Category:Diphosphines]] |
||
[[Category:Named phosphines]] |
|||