X-ray and multinuclear NMR study of the mixed aggregate [(Ph2P(O)N(CH2Ph) CH3)·LiOC6H2- 2,6-{C(CH3)3}2-4- CH3)·C7H8]2: A model for the directed metalation of phosphinamides

Journal of Organometallic Chemistry

Volumn 689, Issue 11, 2004, Pages 1890-1896

  Fernández, Ignacio ^a   Price, Richard D ^b   Bolton, Philip D ^b   Mahon, Mary F ^b   Davidson, Matthew G ^b   López Ortiz, Fernando ^a  

^a UNIVERSITY OF ALMERÍA   (Spain)

^b University of Bath Claverton Down   (United Kingdom)

Author keywords

31P; 7Li coupling; CIPE; Multinuclear magnetic resonance; Phenolate; Phosphinamides; X ray

Indexed keywords

AMIDE; COORDINATION COMPOUND; LITHIUM DERIVATIVE; METAL COMPLEX; OXIDE; PHOSPHINE DERIVATIVE; TOLUENE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL MODEL; COMPLEX FORMATION; CONTROLLED STUDY; CRYSTAL STRUCTURE; DIMERIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID STATE; X RAY CRYSTALLOGRAPHY;

EID: 2342505240     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2004.03.013     Document Type: Article

References (53)

1. Snieckus V. Chem. Rev. 90 1990 879
2. Mugesh G. Singh H.B. Acc. Chem. Res. 35 2002 226
3. Wheatley A.E.H. Eur. J. Inorg. Chem. 3291 2003
4. Beak P. Meyers A.I. Acc. Chem. Res. 19 1986 356
5. Anderson D.R. Faibish N.C. Beak P. J. Am. Chem. Soc. 121 1999 7553
6. Gross K.M.B. Beak P. J. Am. Chem. Soc. 123 2001 315
7. Arvidsson P.I. Hilmersson G. Davidsson O. Helv. Chim. Acta 85 2002 3814
8. Bailey W.F. Beak P. Kerrick S.T. Ma S.H. Wiberg K.B. J. Am. Chem. Soc. 124 2002 1889
9. Van Eikema Hommes N.J.R. Schleyer P.V.R. Angew. Chem. Int. Ed. Engl. 31 1992 755
10. Van Eikema Hommes N.J.R. Schleyer P.V.R. Tetrahedron 50 1994 5903
11. Kremer T. Junge M. Schleyer P.V.R. Organometallics 15 1996 3345
12. Fernández I. López-Ortiz F. Tejerina B. García-Granda S. Org. Lett. 3 2001 1339 1342
13. Fernández I. López-Ortiz F. Menéndez-Velázquez A. García-Granda S. J. Org. Chem. 67 2002 3852
14. Ruiz-Gómez G. López Ortiz F. Synlett 781 2002
15. Fernández I. Forcén-Acebal A. Gracía-Granda S. López-Ortiz F. J. Org. Chem. 68 2003 4472
16. I. Fernández, Ph.D. Thesis, Almería (2003)
17. Fernández, J. González, F. López-Ortiz, A. J. Am. Chem. Soc. (submitted)
18. Setter W. Schleyer P.R. Adv. Organomet. Chem. 24 1985 353
19. Shade C. Schleyer P.R. Adv. Organomet. Chem. 27 1987 169
20. Olsher U. Izatt R.M. Bradshaw J.S. Dalley N.K. Chem. Rev. 91 1991 137
21. Snaith R Wright D.S. in: Sapse A.M. Schleyer P.R. (Eds.), Lithium Chemistry - A Theoretical and Experimental Overview 1995 VCH New York
22. Armstrong D.R. Davidson M.G. Davies R.P. Mitchell H.J. Oakley R.M. Raithby P.R. Snaith R. Warren S. Angew. Chem. Int. Ed. Engl. 35 1996 1942
23. Barr D. Doyle M.J. Mulvey R.E. Raithby P.R. Berd D. Snaith R. Wright D.S. J. Chem. Soc., Chem. Commun. 318 1989
24. Armstrong D.R. Banbury F.A. Davidson M.G. Raithby P.R. Snaith R. Stalke D. J. Chem. Soc., Chem. Commun. 1492 1992
25. Romesberg F.E. Collum D.B. J. Am. Chem. Soc. 116 1994 9198
26. Barker J. Barr D. Barnett N.D.R. Clegg W. Cragg-Hine I. Davidson M.G. Davies R.P. Hodgson S.M. Howard J.A.K. Kilner M. Lehmann C.W. Lopez-Solera I. Mulvey R.E. Raithby P.R. Snaith R. J. Chem. Soc., Dalton Trans. 951 1997
27. Sun X.F. Kenkre S.L. Remenar J.F. Gilchrist J.H. Collum D.B. J. Am. Chem. Soc. 119 1997 4765
28. Shimano M. Meyers A.I. J. Am. Chem. Soc. 116 1994 10815
29. Ye S. Yuan L. Huang Z.Z. Tang Y. Dai L.X. J. Org. Chem. 65 2000 6257
30. Sikorski W.H. Reich H.J. J. Am. Chem. Soc. 123 2001 6527
31. Reich H.J. Sanders A.W. Fieddler A.T. Bevan M.J. J. Am. Chem. Soc. 124 2002 13386
32. Kuchen W. Wunderlich H. Acta Crystallogr. C C56 2000 e434
33. Huffman J.C. Geerts R.L. Gaulton K.G. J. Crystallogr. Spectrosc. Res. 14 1984 541
34. Kociok-Köhn G. Pickardt J. Schumann H. Acta Crystallogr. Sect. C 47 1991 2649
35. Watson K.A. Fortier S. Murchie M.P. Bovenkamp J.W. Rodriguez A. Buchanan G.W. Ratcliffe C.I. Can. J. Chem. 68 1990 1201
36. Boyle T.J. Pedrotty D.M. Alam T.M. Vick S.C. Rodriguez M.A. Inorg. Chem. 39 2000 5133
37. 2)PO fragment: number of observations=26; mean PO bond length=1.482 Å
38. Allen F.H. Acta Crystallogr. B58 2002 380
39. Tebby J.C. in: Verkade J.G. Quin L.D. (Eds.), Phosphorus-31NMR Spectroscopy in Stereochemical Analysis. Organic Compounds and Metal Complexes 1987 VCH Weinheim
40. Seebach D. Siegel H. Gabriel J. Hässig R. Helv. Chim. Acta 63 1980 2046
41. Bauer W. Winchester W.R. Schleyer P.v.R. Organometallics 6 1987 2371
42. Reich H.J. Borst J.P. Dykstra R.R. Green D.P. J. Am. Chem. Soc. 115 1993 8728
43. Reich H.J. Borst J.P. Dykstra R.R. Tetrahedron 50 1994 5869
44. Reich H.J. Holladay J.E. Mason J.D. Sikorski W.H. J. Am. Chem. Soc. 117 1995 12137
45. Reich H.J. Holladay J.E. Walker T.G. Thompson J.L. J. Am. Chem. Soc. 121 1999 9769
46. I. Fernández, F. López-Ortiz, Chem Commun. (submitted)
47. Bacon J. Gillespie R.J. Quail J.W. Can. J. Chem. 41 1963 3063
48. Murali N. Nageswara-Rao B.D. J. Magn. Reson. A 118 1996 202
49. Kofod P.J. Magn. Reson. A 119 1996 219
50. Fraenkel G. Subramanian S. Chow A. J. Am. Chem. Soc. 117 1995 6300
51. We have recently observed the formation of a mixed aggregate constructed by coordination of phosphinamide 1 to a dimer resulting from its benzylic anion. Unpublished results
52. Sheldrick G.M. SHELX-86. Program for the Solution of Crystal Structures 1986 University of Göttingen Germany
53. Sheldrick G.M. SHELX-97. Program for Crystal Structure Refinement 1997 University of Göttingen Germany