Diphenylethylenediamine

Diphenylethylenediamine
Names
IUPAC name
1,2-Diphenyl-1,2-diaminoethane
Other names
DPEN
Identifiers
35132-20-8 YesY
ChEMBL ChEMBL467308 YesY
ChemSpider 5305408 YesY
Jmol interactive 3D Image
PubChem 6931238
Properties
C14H16N2
Molar mass 212.29 g/mol
Appearance White crystals
Melting point 79 to 83 °C (174 to 181 °F; 352 to 356 K)
Slightly
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

1,2-Diphenyl-1,2-ethylenediamine is an organic compound with the 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.[1]

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 resolving agent. In methanol, the R,R enantiomer has an specific rotation of [α]23 +106±1°.

TsDPEN

N-tosylated 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-hydrobenzoin. In this reaction, formate serves as the source of H2:[2]

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 Noyori's 2nd Generation Ruthenium based chiral hydration catalyst, Ryōji Noyori earned the Nobel Prize in 2001.

References

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