| Revision as of 10:29, 12 May 2011 editEmausBot (talk | contribs)Bots, Template editors2,864,855 editsm r2.6.4) (robot Modifying: zh:2,3-双(二苯基膦)丁烷← Previous edit |
Latest revision as of 12:40, 6 May 2021 edit undoLegionMammal978 (talk | contribs)Extended confirmed users7,894 edits add IUPAC name |
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{{chembox |
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| verifiedrevid = 399712576 |
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| ImageFile = Chiraphos.png |
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| verifiedrevid = 428730398 |
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| OtherNames = * (2''S'',3''S'')-(–)-Bis(diphenylphosphino)butane |
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| ImageFile = Chiraphos.svg |
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* (2''R'',3''R'')-(+)-Bis(diphenylphosphino)butane (for the corresponding enantiomer) |
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| ImageFileL2 = Chiraphos-3D-balls-by-AHRLS-2012.png |
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| Section1 = {{Chembox Identifiers |
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| ImageSizeL2 = 140 |
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| ImageFileR2 = Chiraphos-3D-sticks-by-AHRLS-2012.png |
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| ImageSizeR2 = 140 |
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| PIN = ''rel''-bis(diphenylphosphane) |
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| OtherNames = {{ubl|(2''S'',3''S'')-(–)-Bis(diphenylphosphino)butane|(2''R'',3''R'')-(+)-Bis(diphenylphosphino)butane}} |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 8288775 |
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| ChemSpiderID = 8288775 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = FWXAUDSWDBGCMN-ZEQRLZLVSA-N |
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| StdInChIKey = FWXAUDSWDBGCMN-ZEQRLZLVSA-N |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = 74839-84-2 |
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| CASNo = 74839-84-2 |
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| CASNo_Comment = (''R'',''R''-Enantiomer) |
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| CASNo_Comment = (''R'',''R'') |
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| CASNo1_Ref = {{cascite|correct|??}} |
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| CASNo1 = 64896-28-2 |
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| CASNo1 = 64896-28-2 |
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| CASNo1_Comment = (''S'', ''S''-Enantiomer) |
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| CASNo1_Comment = (''S'',''S'') |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 1T086B9Q1J |
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| UNII_Comment = (''R'',''R'') |
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| UNII1_Ref = {{fdacite|correct|FDA}} |
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| UNII1 = 6QR78GZL9B |
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| UNII1_Comment = (''S'',''S'') |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>28</sub>H<sub>28</sub>P<sub>2</sub> |
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| Formula = C<sub>28</sub>H<sub>28</sub>P<sub>2</sub> |
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| Appearance = White powder |
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| Appearance = White powder |
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| MolarMass = 426.47 g/mol |
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| MolarMass = 426.47 g/mol |
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| MeltingPtC = 104 to 109 |
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| MeltingPt = 104–109 °C |
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| Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| GHSPictograms = {{GHS07}} |
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| EUClass = Irritant (XI) |
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| GHSSignalWord = Warning |
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| RPhrases = {{R36/37/38}} |
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| SPhrases = {{S26}} {{S37/39}} |
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| HPhrases = {{H-phrases|315|319|335}} |
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| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}} |
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'''Chiraphos''' is a ] ] employed as a ] in ]. This bidentate ligand chelates metals via the two phosphine groups. Its name is derived from its description — being both ''chiral'' and a ''phosphine''. Chiraphos is available in two enantiomeric forms, ''S'',''S'' and ''R'',''R'', each with C<sub>2</sub> symmetry.<!--meso is not chiraphos--> |
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'''Chiraphos''' is a ] ] employed as a ] in ]. This bidentate ligand chelates metals via the two phosphine groups. Its name is derived from its description — being both ''chiral'' and a ''phosphine''. As a ], chiraphos is available in two enantiomeric forms, ''S'',''S'' and ''R'',''R'', each with C<sub>2</sub> symmetry.<!--meso is not chiraphos--> |
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==Preparation== |
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==Preparation== |
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Chiraphos is prepared from ''S'',''S'' or ''R'',''R''-], which are derived from commercially available ''S'',''S'' or ''R'',''R''-]; the technique of using cheaply available enantiopure starting materials is known as ]. The diol is ] and then the ditosylate is treated with lithium diphenylphosphide.<ref>{{cite journal | author = M. D. Fryzuk, B. Bosnich | title = Asymmetric synthesis. Production of optically active amino acids by catalytic hydrogenation | journal = ] | volume = 99 | year = 1977 | pages = 6262–6267 | doi = 10.1021/ja00461a014 | pmid=893889}}</ref> The ligand was an important demonstration of how the conformation of the chelate ring can affect asymmetric induction by a metal catalyst. Prior to this work, in most chiral phosphines, e.g., ], phosphorus was the stereogenic center.<!--I dont think that this ligand is used for anything anymore--> |
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Chiraphos is prepared from ''S'',''S'' or ''R'',''R''-], which are derived from commercially available ''S'',''S'' or ''R'',''R''-]; the technique of using cheaply available enantiopure starting materials is known as ]. The diol is ] and then the ditosylate is treated with ].<ref name=FryzukBosnich1977>{{cite journal|last1=Fryzuk|first1=M. D.|last2=Bosnich|first2=B.|authorlink2=Brice Bosnich|title=Asymmetric synthesis. Production of optically active amino acids by catalytic hydrogenation|journal=Journal of the American Chemical Society|volume=99|issue=19|year=1977|pages=6262–6267|pmid=893889|doi=10.1021/ja00461a014}}</ref> The ligand was an important demonstration of how the conformation of the chelate ring can affect asymmetric induction by a metal catalyst. Prior to this work, in most chiral phosphines, e.g., ], phosphorus was the stereogenic center.<!--I dont think that this ligand is used for anything anymore--> |
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::]<!--I think that the rxn goes with double inversion--> |
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::]<!--I think that the rxn goes with double inversion--> |
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{{german|Chiraphos|12:39, 21 June 2008 (UTC)}} |
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