Diphenylethylenediamine: Difference between revisions

| verifiedrevid = 399909563

| Name = Diphenylethylenediamine

| ImageFile = dpen.png

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| ImageName =

| IUPACName = 1,2-Diphenyl-1,2-diaminoethane

| OtherNames = DPEN

| Section1 = {{Chembox Identifiers

| SMILES = N[C@@H](c1ccccc1)[C@H](c2ccccc2)N

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| RTECS =

}}

| Section2 = {{Chembox Properties

| Formula = C₁₄H₁₆N₂

| MolarMass = 212.29 g/mol

| Appearance = White [[crystals]]

| Density =

| Solubility = Slightly

| MeltingPt = 79-83 °C

| BoilingPt =

}}

| Section7 = {{Chembox Hazards

| ExternalMSDS =

| MainHazards =

| NFPA-H =

| NFPA-R =

| NFPA-F =

| FlashPt =

| RPhrases =

| SPhrases =

}}

| Section8 = {{Chembox Related

| Function = [[Amine]]

| OtherFunctn =

}}

'''1,2-Diphenyl-1,2-ethylenediamine''' is an [[organic compound]] with the [[chemical formula|formula]] H₂NCHPhCHPhNH₂, where Ph is C₆H₅, phenyl. This diamine is a precursor to a ligand for certain homogeneous hydrogenation catalysts. It can be prepared from benzil by [[reductive amination]].<ref>{{OrgSynth | author = S. Pikul, [[E. J. Corey]]| title = (1R,2R)-(+)- and (1S,2S)-(-)- 1,2-Diphenyl-1,2-Ethylenediamine| collvol = 9| collvolpages = 387 | year = 1998 | prep = CV9P0387}}</ref>

==Optical resolution==

DPEN can be obtained as both the chiral and meso diastereomers, depending on the relative stereochemistry of the two CHPhNH₂ subunits. The chiral diastereomer, which is of greater value, can be resolved into the R,R- and S,S- enantiomers using [[tartaric acid]] as the [[Optical resolution|resolving agent]]. In methanol, the R,R enantiomer has an [[specific rotation]] of [α]₂₃ +106±1°.

==TsDPEN==

N-[[tosyl]]ated derivative, TsDPENH, is a ligand precursor for catalysts for asymmetric [[transfer hydrogenation]]. For example (cymene)Ru(S,S-TsDPEN) catalyzes the [[hydrogenation]] of [[benzil]] into ''R,R''-hydro[[benzoin]]. In this reaction, [[formate]] serves as the source of H₂:<ref>{{OrgSynth | author = Takao Ikariya, Shohei Hashiguchi, Kunihiko Murata, and [[Ryōji Noyori]]| title = Preparation of Optically Active (R,R)-Hydrobenzoin from Benzoin or Benzil| vol = 82 | pages = 10 | year = 2005 | prep = v82p0010}}</ref>

:PhC(O)C(O)Ph + 2 H₂ → PhCH(OH)CH(OH)Ph

This transformation is an example of [[desymmetrization]], the symmetric molecule benzil is converted to the dissymmetric product

==Applications==

DPEN and [[BINAP]] are the key ingredients of [[Ryōji Noyori|Noyori's]] 2^nd Generation [[Ruthenium]] based chiral hydration catalyst, Ryōji Noyori earned the [[Nobel Prize]] in 2001.

<references/>

[[Category:Amines]]

[[Category:Aromatic amines]]