Diphenylethylenediamine

Diphenylethylenediamine
Names
	Preferred IUPAC name 1,2-Diphenylethane-1,2-diamine
	Other names 1,2-Diphenyl-1,2-diaminoethane; DPEN
Identifiers
CAS Number	35132-20-8 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL467308 ;
ChemSpider	5305408 ;
ECHA InfoCard	100.127.996
PubChem CID	6931238;
	InChI InChI=1S/C14H16N2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13-14H,15-16H2/t13-,14-/m0/s1 Key: PONXTPCRRASWKW-KBPBESRZSA-N ; InChI=1/C14H16N2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13-14H,15-16H2/t13-,14-/m0/s1 Key: PONXTPCRRASWKW-KBPBESRZBK;
	SMILES N[C@@H](c1ccccc1)[C@H](c2ccccc2)N;
Properties
Chemical formula	C14H16N2
Molar mass	212.29 g/mol
Appearance	White crystals
Melting point	79 to 83 °C (174 to 181 °F; 352 to 356 K)
Solubility in water	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 a specific rotation of [α]₂₃ +106±1°.

TsDPEN

N-tosylated derivative, TsDPEN, 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]^[3]

PhC(O)C(O)Ph + 2 H₂ → PhCH(OH)CH(OH)Ph (R,R isomer)

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

↑ S. Pikul, E. J. Corey (1998). "(1R,2R)-(+)- and (1S,2S)-(−)- 1,2-Diphenyl-1,2-Ethylenediamine". Organic Syntheses. ; Collective Volume, 9, p. 387
↑ Takao Ikariya, Shohei Hashiguchi, Kunihiko Murata, and Ryōji Noyori (2005). "Preparation of Optically Active (R,R)-Hydrobenzoin from Benzoin or Benzil". Organic Syntheses: 10.
↑ Fei Chen; Zi-Yuan Ding; Yan-Mei He; Qing-Hua Fan (2015). "Synthesis of Optically Active 1,2,3,4-Tetrahydroquinolines via Asymmetric Hydrogenation Using Iridium-Diamine Catalyst". Org. Synth. 92: 213. doi:10.15227/orgsyn.092.0213.

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[1] S. Pikul, E. J. Corey (1998). "(1R,2R)-(+)- and (1S,2S)-(−)- 1,2-Diphenyl-1,2-Ethylenediamine". Organic Syntheses. ; Collective Volume, 9, p. 387

[2] Takao Ikariya, Shohei Hashiguchi, Kunihiko Murata, and Ryōji Noyori (2005). "Preparation of Optically Active (R,R)-Hydrobenzoin from Benzoin or Benzil". Organic Syntheses: 10.

[3] Fei Chen; Zi-Yuan Ding; Yan-Mei He; Qing-Hua Fan (2015). "Synthesis of Optically Active 1,2,3,4-Tetrahydroquinolines via Asymmetric Hydrogenation Using Iridium-Diamine Catalyst". Org. Synth. 92: 213. doi:10.15227/orgsyn.092.0213.