Download PDF
Synthesis 2007(24): 3863-3867  
DOI: 10.1055/s-2007-990868
PAPER
© Georg Thieme Verlag Stuttgart · New York

Efficient Synthesis of Novel N-Substituted Bulky Diphosphinoamines

Munaka C. Maumela*a, Kevin Blanna, Henriëtte de Boda, John T. Dixona, William F. Gabriellia, D. Bradley G. Williamsb
a Sasol Technology (Pty) Ltd, R & D Division, 1 Klasie Havenga Road, Sasolburg 1947, South Africa
Fax: +27(11)5220784; e-Mail: chris.maumela@sasol.com;
b University of Johannesburg, P.O. Box 524, Auckland Park 2006, South Africa
Further Information

Publication History

Received 2 August 2007
Publication Date:
31 October 2007 (online)

    Permissions and Reprints All articles of this category

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 
    CrossrefSearch in Google Scholar
  • 2 Keim W. Kowaldt FH. Goddard R. Krueger C. Angew. Chem., Int. Ed. Engl.  1978,  17:  466 ; Angew. Chem. 1978, 90, 493
    CrossrefSearch in Google Scholar
  • 3a Wass DF. inventors; (BP Chemicals Ltd) Pat. Appl. WO  02/04119.  ; Chem. Abstr. 2001, 136, 86240
    Crossref
  • 3b Carter A. Cohen SA. Cooley NA. Murphy A. Scutt J. Wass DF. Chem. Commun.  2002,  858 
    Crossref
  • 3c Skupinska J. Chem. Rev.  1991,  91:  613 
    CrossrefSearch in Google Scholar
  • 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 
    CrossrefSearch in Google Scholar
  • 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 
    CrossrefSearch in Google Scholar
  • 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
    Crossref
  • 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
    Crossref
  • 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 
    Crossref
  • 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 
    Crossref
  • 4g Walsh R. Morgan DH. Bollmann A. Dixon JT. App. Catal. A: Gen.  2006,  306:  184 
    CrossrefSearch in Google Scholar
  • 4h Kuhlmann S. Dixon JT. Haumann M. Morgan DH. Ofili J. Spuhl O. Taccardi N. Wasserscheid P. Adv. Synth. Catal.  2006,  348:  1200 
    CrossrefSearch in Google Scholar
  • 5 An excellent general overview is provided by: Vogt D. In Applied Homogeneous Catalysis with Organometallic Compounds   Vol. 1:  Cornils B. Herrmann WA. Wiley-VCH; New York: 2002.  p.240 
    Search in Google Scholar
  • 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 
    CrossrefSearch in Google Scholar
  • 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 
    CrossrefSearch in Google Scholar
  • 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 
    CrossrefSearch in Google Scholar
  • 7a Appleby T. Woollins DJ. Coord. Chem. Rev.  2002,  235:  121 
    CrossrefSearch in Google Scholar
  • 7b Balakrishna MS. Sreenivasa Reddy V. Krishnamurthy SS. Nixon JF. Burckett St. Laurent JCTR. Coord. Chem. Rev.  1994,  129:  1 
    CrossrefSearch in Google Scholar
  • 7c Dyson PJ. Coord. Chem. Rev.  2005,  2056 
    Crossref
  • 7d Woollins DJ. Polyhedron  1995,  14:  3367 
    CrossrefSearch in Google Scholar
  • 7e Balakrishna MS. Prakasha TK. Krishnamurthy SS. Siriwardane U. Hosmane NS. J. Organomet. Chem.  1990,  203 
    Crossref
  • 7f Ewart G. Lane P. McKenzie JC. Payne DS. J. Chem. Soc.  1964,  1543 
    Crossref
  • 7g Cross RJ. Green TH. Keat R. J. Chem. Soc.  1976,  1425 
    Crossref
  • 7h Gaw KG. Smith MB. Slawin MZ. New J. Chem.  2000,  24:  429 
    CrossrefSearch in Google Scholar
  • 7i Elowe PR. McCann C. Pringle PG. Spitzmesser SK. Bercaw JE. Organometallics  2006,  25:  5255 
    CrossrefSearch in Google Scholar
  • 7j Gaw KG. Smith MB. Steed JW. J. Organomet. Chem.  2002,  664:  294 
    CrossrefSearch in Google Scholar
  • 7k Schmidbaur H. Lauteschlager S. Kohler FH. J. Organomet. Chem.  1984,  271:  1 
    CrossrefSearch in Google Scholar
  • 8 Foss VL. Veits YuA. Chernykh TE. Lutsenko IF. Zh. Obshch. Khim.  1984,  54:  2670 ; Chem. Abstr. 1985, 103, 37537
    Search in Google Scholar
  • 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 
    CrossrefSearch in Google Scholar
9

1H NMR (CDCl3): δ = 1.35 (s, 9 H, t-C4H9), 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).

12

N,N-Bis(diisopropylphosphanyl)ethylamine: 31P NMR (162 MHz, CDCl3): δ = 83.9 (s).