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Revision as of 16:20, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,055 edits Saving copy of the {{chembox}} taken from revid 475471115 of page 1,3-Bis(diphenylphosphino)propane for the Chem/Drugbox validation project (updated: '').		Latest revision as of 12:36, 28 September 2023 edit Mykhal (talk | contribs)Extended confirmed users5,594 editsm expand summ. chem. formula
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	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
	{{chembox		{{chembox
		⚫	|verifiedrevid = 477204968
	| Verifiedfields = changed
		⚫	|ImageFile=Dppp.svg
⚫	| verifiedrevid = 456367575
⚫	|ImageFile=Dppp.png
	|ImageSize=200px		|ImageSize=200px
	|ImageFile1=Dppp-from-xtal-2005-3D-balls.png		|ImageFile1=Dppp-from-xtal-2005-3D-balls.png
	|IUPACName=Propane-1,3-diylbis(diphenylphosphane)		|PIN=(Propane-1,3-diyl)bis(diphenylphosphane)
	|OtherNames=
	|Section1={{Chembox Identifiers		|Section1={{Chembox Identifiers
	| Abbreviations = DPPP		|Abbreviations = DPPP
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 73276		|ChemSpiderID = 73276
	| InChI = 1/C27H26P2/c1-5-14-24(15-6-1)28(25-16-7-2-8-17-25)22-13-23-29(26-18-9-3-10-19-26)27-20-11-4-12-21-27/h1-12,14-21H,13,22-23H2		|InChI = 1/C27H26P2/c1-5-14-24(15-6-1)28(25-16-7-2-8-17-25)22-13-23-29(26-18-9-3-10-19-26)27-20-11-4-12-21-27/h1-12,14-21H,13,22-23H2
	| InChIKey = LVEYOSJUKRVCCF-UHFFFAOYAP		|InChIKey = LVEYOSJUKRVCCF-UHFFFAOYAP
	| SMILES1 = c1ccc(cc1)P(CCCP(c2ccccc2)c3ccccc3)c4ccccc4		|SMILES1 = c1ccc(cc1)P(CCCP(c2ccccc2)c3ccccc3)c4ccccc4
	| ChEMBL_Ref = {{ebicite|changed|EBI}}		|ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 73394		|ChEMBL = 73394
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C27H26P2/c1-5-14-24(15-6-1)28(25-16-7-2-8-17-25)22-13-23-29(26-18-9-3-10-19-26)27-20-11-4-12-21-27/h1-12,14-21H,13,22-23H2		|StdInChI = 1S/C27H26P2/c1-5-14-24(15-6-1)28(25-16-7-2-8-17-25)22-13-23-29(26-18-9-3-10-19-26)27-20-11-4-12-21-27/h1-12,14-21H,13,22-23H2
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = LVEYOSJUKRVCCF-UHFFFAOYSA-N		|StdInChIKey = LVEYOSJUKRVCCF-UHFFFAOYSA-N
	| CASNo_Ref = {{cascite|correct|CAS}}		|CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo=6737-42-4		|CASNo=6737-42-4
			|UNII_Ref = {{fdacite|correct|FDA}}
⚫	| PubChem=81219
			|UNII = 44R56E2C68
⚫	| SMILES = P(c1ccccc1)(c2ccccc2)CCCP(c3ccccc3)c4ccccc4
		⚫	|PubChem=81219
		⚫	|SMILES = P(c1ccccc1)(c2ccccc2)CCCP(c3ccccc3)c4ccccc4
	}}		}}
	|Section2={{Chembox Properties		|Section2={{Chembox Properties
	| C = 27 | H = 26 | P = 2		|C=27 | H=26 | P=2
	| Appearance= white solid		|Appearance= white solid
		⚫	|Solubility= chlorocarbons
	| Density=
	| MeltingPt=
	| BoilingPt=
⚫	| Solubility= chlorocarbons
⚫	}}
	|Section3={{Chembox Hazards
	| MainHazards=
	| FlashPt=
	| Autoignition=
	}}
	}}		}}
		⚫	}}
			'''1,3-Bis(diphenylphosphino)propane''' ('''dppp''') is an ] with the formula Ph{{sub|2}}P(CH{{sub|2}}){{sub|3}}PPh{{sub|2}}. The compound is a white solid that is soluble in organic solvents. It is slightly ], degrading in air to the ]. It is classified as a ] in ] and ].
			The diphosphine can be prepared by the reaction of ] and 1,3-dichloropropane (Ph = C{{sub|6}}H{{sub|5}}):
			: 2 Ph{{sub|2}}PLi + Cl(CH{{sub|2}}){{sub|3}}Cl → Ph{{sub|2}}P(CH{{sub|2}}){{sub|3}}PPh{{sub|2}} + 2 LiCl
			However, it can be synthesised via a much more controllable (and cheaper) route, via metal-halogen exchange and then metathesis:
			:Br(CH{{sub|2}}){{sub|3}}Br + 2 {{sup|t}}BuLi → Li(CH{{sub|2}}){{sub|3}}Li + 2 {{sup|t}}BuBr
			:Li(CH{{sub|2}}){{sub|3}}Li + 2 PCl{{sub|3}} → Cl{{sub|2}}P(CH{{sub|2}}){{sub|3}}PCl{{sub|2}} + 2 LiCl
			:Cl{{sub|2}}P(CH{{sub|2}}){{sub|3}}PCl{{sub|2}} + 4 PhLi → Ph{{sub|2}}P(CH{{sub|2}}){{sub|3}}PPh{{sub|2}} + 4 LiCl
			==Coordination chemistry and use as co-catalyst==
			The diphosphine serves as a ] forming six-membered C{{sub|3}}P{{sub|2}}M chelate ring with a natural ] of 91°.<ref name="vanLeeuwen">{{cite journal |last1=Birkholz (née Gensow) |first1=Mandy-Nicole |last2=Freixa |first2=Zoraida |last3=van Leeuwen |first3=Piet W. N. M. |title=Bite angle effects of diphosphines in C–C and C–X bond forming cross coupling reactions |journal=Chemical Society Reviews |date=2009 |volume=38 |issue=4 |pages=1099–1118 |doi=10.1039/B806211K |pmid=19421583}}</ref> For example, the complex ] is prepared by combining equimolar portions of the ligand and ] hexahydrate. This nickel complex serves as a catalyst for the ] reaction.<ref name = kumada>{{OrgSynth | author = Kumada, Makota | author2 = Tamao, Kohei | author3 = Sumitani, Koji | title = Phosphine-Nickel Complex Catalyzed Cross-Coupling of Grignard Reagents with Aryl and Alkenyl Halides: 1,2-dibutylbenzene | collvol = 6 | collvolpages = 407 | year = 1988 | prep = cv6p0407}}</ref> Dppp is also used as a ligand for ](II) catalysts to co-polymerize ] and ] to give ]s.<ref>{{cite encyclopedia | doi = 10.1002/0471440264.pst273 | encyclopedia = Encyclopedia Of Polymer Science and Technology | title = Polyketones | year = 2001 | last1 = Drent | first1 = E. | last2 = Mul | first2 = W. P. | last3 = Smaardijk | first3 = A. A.| isbn = 9781118633892 }}</ref> Dppp can sometimes be used in palladium-catalyzed arylation under ] conditions to control regioselectivity.<ref>Cabri, Walter; Candiani, Ilaria; Bedeschi Angelo; Penco, Sergio"α-Regioselectivity in Palladium-Catalyzed Arylation of Acyclic Enol Ethers" journal= Journal of Organic Chemistry, 1991, volume 57, p. 1481. {{doi|10.1021/jo00031a029}}</ref>
			==References==
			{{Reflist}}
			{{DEFAULTSORT:Bis(diphenylphosphino)propane, 1, 3-}}
			]
			]