Ortho-Lithiated benzyl diorganophosphines [o-(R2PCH2)C6H4Li(Et2O)], R=Ph, Me. Synthesis, structural characterization, and reactions

Journal of Organometallic Chemistry

Volumn 622, Issue 1-2, 2001, Pages 121-134

  Müller, Gerhard ^a   Abicht, Hans Peter ^b   Waldkircher, Martin ^a   Lachmann, Joachim ^a   Lutz, Martin ^a   Winkler, Martin ^a  

^a UNIVERSITY OF KONSTANZ   (Germany)

^b MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

Author keywords

Anionic benzyl phosphines; Crystal structure elucidation; Lithium organyls

Indexed keywords

EID: 0041878692     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(00)00885-8     Document Type: Article

References (100)

1. Abicht H.-P., Issleib K. Z. Anorg. Allg. Chem. 422:1976;237.
2. Abicht H.-P., Issleib K. Z. Anorg. Allg. Chem. 447:1978;53.
3. (a) H.-P. Abicht, R. Barth, K. Peters, E.-M. Peters, H.-G. von Schnering, Z. Chem. 26 (1986) 409.
4. (b) K. Peters, E.-M. Peters, H.-G. von Schnering, H.-P. Abicht, Z. Kristallogr. 171 (1985) 313.
5. (c) H.-P. Abicht, K. Issleib, J. Organomet. Chem. 289 (1985) 201.
6. (d) H.-P.Abicht, Z. Chem. 25 (1985) 318 and references cited therein.
7. (e) H.-P. Abicht, Z. Chem. 24 (1984) 387.
8. (f) H.-P. Abicht, P. Lehninger, K. Issleib, J. Organomet. Chem. 250 (1983) 609.
9. (g) H.-P. Abicht, U. Baumeister, H. Hartung, K. Issleib, R.A. Jacobson, J. Richardson, S.M. Socol, J.G. Vercade, Z. Anorg. Allg. Chem. 494 (1982) 55.
10. (h) H.-P. Abicht, K. Issleib, Z. Chem. 21 (1981) 341 and references cited therein.
11. (a) G. Müller, J. Lachmann, Z. Naturforsch. 48b (1993) 1544.
12. (b) G. Müller, J. Lachmann, Z. Naturforsch. 48b (1993) 1248.
13. (c) H. Handwerker, M. Paul, J. Blümel, C. Zybill, Angew. Chem., 105 (1993) 1375; Angew. Chem. Int. Ed. Engl., 32 (1993) 1313.
14. (c) H. Handwerker, M. Paul, J. Blümel, C. Zybill, Angew. Chem., 105 (1993) 1375; Angew. Chem. Int. Ed. Engl., 32 (1993) 1313.
15. (d) G. Müller, J. Lachmann, A. Rufinska, Organometallics 11 (1992) 2970.
16. (e) G. Müller, J. Lachmann, J. Riede, Z. Naturforsch. 47b (1992) 823.
17. (f) H.G. Ang, B. Chang, W.L. Kwik, J. Chem. Soc., Dalton Trans. (1992) 2161.
18. (g) G. Reber, J. Riede, G. Müller, Z. Naturforsch. 43b (1988) 915.
19. (h) H.-P. Abicht, K. Jurkschat, Z. Chem. 28 (1988) 222.
20. (i) H.-P. Abicht, K. Jurkschat, A. Tzschach, K. Peters, E.-M. Peters, H.-G. von Schnering, J. Organomet. Chem. 326 (1987) 357.
21. (j) K. Jurkschat, H.-P. Abicht, A. Tzschach, B. Mahieu, J. Organomet. Chem. 309 (1986) C47.
22. (k) H.-P. Abicht, K. Issleib, Z. Chem. 24 (1984) 414.
23. (l) H.-P. Abicht, C. Mügge, H. Weichmann, Z. Anorg. Allg. Chem. 467 (1980) 203.
24. Müller G., Waldkircher M., Winkler M. Z. Naturforsch. 49b:1994;1606.
25. Zimmermann H., Burzlaff H. Z. Kristallogr. 170:1985;241.
26. LePage Y. J. Appl. Crystallogr. 15:1982;255.
27. Sheldrick G.M. Sheldrick G.M., Krüger C., Goddard R. Crystallographic Computing 3. 1985;175 Oxford University Press, Oxford.
28. Cromer D.T., Waber J.T. Acta Crystallogr. 18:1965;104.
29. Stewart R.F., Davidson E.R., Simpson W.T. J. Chem. Phys. 42:1965;3175.
30. International Tables for Crystallography, vol. IV, Kynoch, Birmingham, UK, 1974.
31. G.M. Sheldrick, SHELXL-93, Program for the Refinement of Crystal Structures, Universitity of Göttingen, Germany, 1993.
32. (a) C.K. Johnson, M.N. Burnett, ORTEP-III (version 1.0.2), Rep. ORNL-6895, Oak Ridge National Laboratory, Oak Ridge, TN, USA, 1996.
33. (b) Windows version, L. J. Farrugia, University of Glasgow, Glasgow, Scotland, UK, 1999.
34. (a) A.L. Spek, PLATON, A Multipurpose Crystallographic Tool, Utrecht University Utrecht, The Netherlands, 2000.
35. (b) See also: A.L. Spek, Acta Crystallogr. Sect. A 46 (1990) C34.
36. (a) D.J. Peterson, Organomet. Chem. Rev. A 7 (1972) 295.
37. (b) See also: T.F. Crimmins, E.M. Rather, J. Org. Chem. 43 (1978) 2170.
38. (c) W.H. Puterbaugh, C.R. Hauser, J. Am. Chem. Soc. 85 (1963) 2467.
39. (a) G. Müller, M. Lutz, M. Waldkircher, Acta Crystallogr. Sect. C 52 (1996) 1182.
40. (b) W. Zarges, M. Marsch, K. Harms, G. Boche, Chem. Ber. 122 (1989) 2303.
41. (c) M.A. Beno, H. Hope, M.M. Olmstead, P.P. Power, Organometallics 4 (1985) 2117.
42. (d) L.M. Engelhardt, W.-P. Leung, C.L. Raston, P. Twiss, A.H. White, J. Chem. Soc. Dalton Trans. (1984) 321.
43. (e) G. Boche, G. Decker, H. Etzrodt, H. Dietrich, W. Mahdi, A.J. Kos, P. von R. Schleyer, J. Chem. Soc. Chem. Commun. (1984) 1493.
44. (f) S.P. Patterman, I.L. Karle, G.D. Stucky, J. Am. Chem. Soc. 92 (1970) 1150.
45. (g) For a theoretical treatment see: A. Sygula, P.W. Rabideau, J. Am. Chem. Soc. 114 (1992) 821.
46. Decken A., Cowley A.H. J. Organomet. Chem. 509:1996;135.
47. L.M. Engelhardt, G.E. Jacobsen, C.L. Raston, A.H. White, J. Chem. Soc. Chem. Commun. (1984) 220.
48. L.T. Byrne, L.M. Engelhardt, G.E. Jacobsen, W.-P. Leung, R.I. Papasergio, C.L. Raston, B.W. Skelton, P Twiss, A.H. White, J. Chem. Soc. Dalton Trans. (1989) 105.
49. Fraenkel G., Winchester W.R., Williard P.G. Organometallics. 8:1989;2308.
50. Blaurock S., Kühl O., Hey-Hawkins E. Organometallics. 16:1997;807.
51. A. Pape, M. Lutz, G. Müller, Angew. Chem. 106 (1994) 2375; Angew. Chem. Int. Ed. Engl. 33 (1994) 2281.
52. A. Pape, M. Lutz, G. Müller, Angew. Chem. 106 (1994) 2375; Angew. Chem. Int. Ed. Engl. 33 (1994) 2281.
53. (a) D. Thoennes, E. Weiss, Chem. Ber. 111 (1978) 3157.
54. (b) Review: E. Weiss, Angew. Chem. 105 (1993) 1565; Angew. Chem. Int. Ed. Engl. 32 (1993) 1501.
55. (b) Review: E. Weiss, Angew. Chem. 105 (1993) 1565; Angew. Chem. Int. Ed. Engl. 32 (1993) 1501.
56. For ortho-lithiated benzyl amines a substantial amount of spectroscopic and structural information is also at hand: (a) H.J. Reich, B.Ö. Gudmundsson, J. Am. Chem. Soc. 118 (1996) 6074.
57. (b) M.P.H. Rietveld, I.C.M. Wehman-Ooyevaar, G.M. Capteijn, D.M. Grove, W.J.J. Smeets, H. Kooijman, A.L. Spek, G. van Koten, Organometallics 13 (1994) 3782.
58. (c) I.C.M. Wehman-Ooyevaar, G.M. Capteijn, D.M. Grove, A.L. Spek, G. van Koten, J. Organomet. Chem. 452 (1993) C1.
59. (d) E. Wehman, J.T.B.H. Jastrzebski, J.-M. Ernsting, D.M. Grove, G. van Koten, J. Organomet. Chem. 353 (1988) 145.
60. (e) W.J.J.Smeets, A.L. Spek, A.A.H. van der Zeijden, G. van Koten, Acta Crystallogr. Sect. C 43 (1987) 1429.
61. (f) J.T.B.H. Jastrzebski, G. van Koten, M. Konijn, C.H. Stam, J. Am. Chem. Soc. 104 (1982) 5490.
62. (g) F.T. Oakes, J.F. Sebastian, J. Organomet. Chem. 159 (1978) 363.
63. 6: J.F. Malone, W.S. McDonald, J. Chem. Soc. Chem. Commun. (1967) 444.
64. Review: K. Izod, Adv. Inorg. Chem. 50 (2000) 33.
65. (a) S. Harder, P.F. Ekhart, L. Brandsma, J.A. Kanters, A.J.M. Duisenberg, P. von R. Schleyer, Organometallics 11 (1992) 2623 and references cited therein.
66. (b) See also the following leading references: G. Girolami, M.E. Riehl, K.S. Suslick, S.R. Wilson, Organometallics 11 (1992) 3907.
67. (c) T. Maetzke, D. Seebach, Helv. Chim. Acta 72 (1989) 624.
68. (d) U. Schümann, J. Kopf, E. Weiss, Angew. Chem. 97 (1985) 222; Angew. Chem. Int. Ed. Engl. 24 (1985) 215.
69. (d) U. Schümann, J. Kopf, E. Weiss, Angew. Chem. 97 (1985) 222; Angew. Chem. Int. Ed. Engl. 24 (1985) 215.
70. (e) H. Hope, P.P. Power, J. Am. Chem. Soc. 105 (1983) 5320.
71. 2Ph], and its crystal and molecular structure was determined. See ref. [16a].
72. nBu in the presence of tmeda: (a) A. Feustel, unpublished results.
73. (b) See also: V. Knapp, M. Winkler, G. Müller, Z. Naturforsch. B, 55b (2000) 1114.
74. Zarges W., Marsch M., Harms K., Koch W., Frenking G., Boche G. Chem. Ber. 124:1991;543.
75. (a) L.M. Engelhardt, W.-P. Leung, C.L. Raston, A.H. White, J. Chem. Soc. Dalton Trans. (1985) 337.
76. (b) W.-P. Leung, C.L. Raston, B.W. Skelton, A.H. White, J. Chem. Soc. Dalton Trans. (1984) 1801.
77. (c) M.F. Lappert, C.L. Raston, B.W. Skelton, A.H. White, J. Chem. Soc. Chem. Commun. (1982) 14.
78. Pyridine derivatives: (a) R. Hacker, P. von R. Schleyer, G. Reber, G. Müller, L. Brandsma, J. Organomet. Chem. 316 (1986) C4.
79. (b) D. Colgan, R.I. Papasergio, C.L. Raston, A.H. White, J. Chem. Soc. Chem. Commun. (1984) 1708.
80. (c) R.I. Papasergio, C.L. Raston, A.H. White, J. Chem. Soc. Chem. Commun. (1983) 1419.
81. M. Winkler, M. Lutz, G. Müller, Angew. Chem. 106 (1994) 2375; Angew. Chem. Int. Ed. Engl. 33 (1994) 2279.
82. M. Winkler, M. Lutz, G. Müller, Angew. Chem. 106 (1994) 2375; Angew. Chem. Int. Ed. Engl. 33 (1994) 2279.
83. (a) R. Amstutz, T. Laube, W.B. Schweizer, D. Seebach, J.D. Dunitz, Helv. Chim. Acta 67 (1984) 224.
84. (b) R. Amstutz, J.D. Dunitz, D. Seebach, Angew. Chem. 93 (1981) 487; Angew. Chem. Int. Ed. Engl. 20 (1981) 464.
85. (b) R. Amstutz, J.D. Dunitz, D. Seebach, Angew. Chem. 93 (1981) 487; Angew. Chem. Int. Ed. Engl. 20 (1981) 464.
86. Steinborn D., Neumann O., Weichmann H., Heinemann F.W., Wagner J.-P. Polyhedron. 17:1998;351.
87. Boche G., Marsch M., Harbach J., Harms K., Ledig B., Schubert F., Lohrenz J.C.W., Ahlbrecht H. Chem. Ber. 126:1993;1887.
88. (a) G. Boche, F. Bosold, J.C.W.Lohrenz, A. Opel, P. Zulauf, Chem. Ber. 126 (1993) 1873.
89. (b) G. Boche, A. Opel, M. Marsch, K. Harms, F. Haller, J.C.W. Lohrenz, C. Thümmler, W. Koch, Chem. Ber. 125 (1992) 2265.
90. (c) G. Boche, F. Bosold, P. Zulauf, M. Marsch, K. Harms, J.C.W. Lohrenz, Angew. Chem. 103 (1991) 1497; Angew. Chem. Int. Ed. Engl. 30 (1991) 1455.
91. (c) G. Boche, F. Bosold, P. Zulauf, M. Marsch, K. Harms, J.C.W. Lohrenz, Angew. Chem. 103 (1991) 1497; Angew. Chem. Int. Ed. Engl. 30 (1991) 1455.
92. (d) S. Harder, J. Boersma, L. Brandsma, J.A. Kanters, W. Bauer, R. Pi, P. von R. Schleyer, H. Schöllhorn, U. Thewalt, Organometallics 8 (1989) 1688.
93. (a) E. Nietzschmann, O. Böge, J. Heinicke, A. Tzschach, Z. anorg. allg. Chem. 588 (1990) 192.
94. (b) E. Nietzschmann, O. Böge, M. Dargatz, J. Heinicke, R. Kadyrov, A. Tzschach, Z. Anorg. Allg. Chem. 588 (1990) 51.
95. (c) D. Hellwinkel, R. Lenz, Chem. Ber. 118 (1985) 66.
96. Wykypiel W., Lehmann J.-J., Seebach D. Helv. Chim. Acta. 64:1981;1337.
97. Abicht H.-P., Schmidt H., Issleib K. Z. Chem. 25:1985;410.
98. 2Ti-benzyl complexes have been found to undergo reductive eliminations under hydrogen abstraction from the Cp-rings to form tolyl species: (a) G. Fachinetti, C. Floriani, J. Chem. Soc. Chem. Commun. (1972) 654.
99. (b) C.P. Boekel, J.H.Teuben, H.J. de Liefde Meijer, J. Organomet. Chem. 102 (1975) 317.
100. (c) G.J. Erskine, D.A. Wilson, J.D. McCowan, J. Organomet. Chem. 114 (1976) 119.