Abstract
A convenient procedure for the facile preparation of electron-rich bulky diphosphinoamines from alkylamines and chlorodiphenylphosphine has been developed. The choice of solvent proved to be critical to the successful synthesis of the diphosphinoamine (PNP) products.
Key words
alkylamines - ethylene oligomerisation catalysis - solvent effects - diphoshinoamine ligands - steric hindrance
References
1 Al-Jarallah AM.
Anabtawi JA.
Siddiqui MAB.
Aitani AM.
Al-Sa’doun AW.
Catal. Today
1992,
14:
1
2 Keim W.
Kowaldt FH.
Goddard R.
Krueger C.
Angew. Chem., Int. Ed. Engl.
1978,
17:
466 ; Angew. Chem. 1978 , 90 , 493
3a Wass DF. inventors; (BP Chemicals Ltd) Pat. Appl. WO 02/04119.
; Chem. Abstr. 2001 , 136, 86240
3b Carter A.
Cohen SA.
Cooley NA.
Murphy A.
Scutt J.
Wass DF.
Chem. Commun.
2002,
858
3c Skupinska J.
Chem. Rev.
1991,
91:
613
4a Bollmann A.
Blann K.
Dixon JT.
Hess FM.
Killian E.
Maumela H.
McGuinness DS.
Morgan DH.
Nevelling A.
Otto S.
Overett MJ.
Slawin AZM.
Wasserscheid P.
Kuhlmann S.
J. Am. Chem. Soc.
2004,
126:
14712
4b Overett MJ.
Blann K.
Bollmann A.
Dixon JT.
Haasbroek D.
Killian E.
Maumela H.
McGuinness DS.
Morgan DH.
J. Am. Chem. Soc.
2005,
127:
10723
4c Blann K, Bollmann A, Neveling A, Morgan DH, Maumela H, Killian E, Hess FM, Otto S, Pepler L, Mohamed HA, and Overett MJ. inventors; [Sasol Technology (Pty) Ltd.] Pat. Appl. WO 2004/056479.
; Chem. Abstr. 2004 , 141, 89548
4d Blann K, Bollmann A, Neveling A, Morgan DH, Maumela H, Killian E, Hess FM, Otto S, Pepler L, Mohamed HA, and Overett MJ. inventors; [Sasol Technology (Pty) Ltd.], Pat. Appl. WO 2004/056477.
; Chem. Abstr. 2004 , 141, 89536
4e Blann K.
Bollmann A.
Dixon JT.
Hess FM.
Killian E.
Maumela H.
Morgan DH.
Neveling A.
Otto S.
Overett MJ.
Chem. Commun.
2005,
620
4f Overett MJ.
Blann K.
Bollmann A.
Dixon JT.
Hess FM.
Killian E.
Maumela H.
Morgan DH.
Neveling A.
Otto S.
Chem. Commun.
2005,
622
4g Walsh R.
Morgan DH.
Bollmann A.
Dixon JT.
App. Catal. A: Gen.
2006,
306:
184
4h Kuhlmann S.
Dixon JT.
Haumann M.
Morgan DH.
Ofili J.
Spuhl O.
Taccardi N.
Wasserscheid P.
Adv. Synth. Catal.
2006,
348:
1200
5 Vogt D. In Applied Homogeneous Catalysis with Organometallic Compounds
Vol. 1:
Cornils B.
Herrmann WA.
Wiley-VCH;
New York:
2002.
p.240
6a Blann K.
Bollmann A.
de Bod H.
Dixon JT.
Killian E.
Klaas P.
Maumela MC.
Maumela H.
McConnell AE.
Morgan DH.
Overett MJ.
Prétorius M.
Kuhlmann S.
Wasserscheid P.
J. Catal.
2007,
249:
242
6b Kuhlmann S.
Blann K.
Bollmann A.
Dixon JT.
Killian E.
Maumela MC.
Maumela H.
Morgan DH.
Prétorius M.
Taccardi N.
Wasserscheid P.
J. Catal.
2007,
245:
277
6c Killian E.
Blann K.
Bollmann A.
Dixon JT.
Kuhlmann S.
Maumela MC.
Maumela H.
Morgan DH.
Nongodlwana P.
Overett MJ.
Pretorius M.
Höfener K.
Wasserscheid P.
J. Mol. Catal. A: Chem.
2007,
270:
214
7a Appleby T.
Woollins DJ.
Coord. Chem. Rev.
2002,
235:
121
7b Balakrishna MS.
Sreenivasa Reddy V.
Krishnamurthy SS.
Nixon JF.
Burckett St. Laurent JCTR.
Coord. Chem. Rev.
1994,
129:
1
7c Dyson PJ.
Coord. Chem. Rev.
2005,
2056
7d Woollins DJ.
Polyhedron
1995,
14:
3367
7e Balakrishna MS.
Prakasha TK.
Krishnamurthy SS.
Siriwardane U.
Hosmane NS.
J. Organomet. Chem.
1990,
203
7f Ewart G.
Lane P.
McKenzie JC.
Payne DS.
J. Chem. Soc.
1964,
1543
7g Cross RJ.
Green TH.
Keat R.
J. Chem. Soc.
1976,
1425
7h Gaw KG.
Smith MB.
Slawin MZ.
New J. Chem.
2000,
24:
429
7i Elowe PR.
McCann C.
Pringle PG.
Spitzmesser SK.
Bercaw JE.
Organometallics
2006,
25:
5255
7j Gaw KG.
Smith MB.
Steed JW.
J. Organomet. Chem.
2002,
664:
294
7k Schmidbaur H.
Lauteschlager S.
Kohler FH.
J. Organomet. Chem.
1984,
271:
1
8 Foss VL.
Veits YuA.
Chernykh TE.
Lutsenko IF.
Zh. Obshch. Khim.
1984,
54:
2670 ; Chem. Abstr. 1985 , 103, 37537
9
1 H NMR (CDCl3 ): δ = 1.35 (s, 9 H, t- C4 H9 ), 2.10 (d, J = 11.6 Hz, 1 H, NH), 7.27-7.36 (m, 6 H, ArH), 7.40-7.45 (m, 4 H, ArH).
10 Fei Z.
Scopelliti R.
Dyson PJ.
J. Chem. Soc., Dalton Trans.
2003,
2772
11 Biricik N.
Fei Z.
Scopelliti R.
Dyson PJ.
Helv. Chim. Acta
2003,
86:
3281
12
N ,N -Bis(diisopropylphosphanyl)ethylamine: 31 P NMR (162 MHz, CDCl3 ): δ = 83.9 (s).
