An ab initio study on dilithiosulfoximines

Journal of Organometallic Chemistry

Volumn 584, Issue 1, 1999, Pages 27-32

  Müller, Jürgen F K ^a   Batra, Rohit ^a  

^a UNIVERSITY OF BASEL   (Switzerland)

Author keywords

Ab initio calculations; Dianions; Gas phase structures; Lithium; Sulfoximines

Indexed keywords

EID: 0038286635     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(99)00081-9     Document Type: Article

References (80)

1. Reviews: (a) J.D. Morrison, Asymmetric Synthesis, vol. 5, Academic Press, New York, 1985. (b) R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994. (c) G.R. Stephenson, Advanced Asymmetric Synthesis, Chapman and Hall, London, 1996.
2. Reviews: (a) J.D. Morrison, Asymmetric Synthesis, vol. 5, Academic Press, New York, 1985. (b) R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994. (c) G.R. Stephenson, Advanced Asymmetric Synthesis, Chapman and Hall, London, 1996.
3. Reviews: (a) J.D. Morrison, Asymmetric Synthesis, vol. 5, Academic Press, New York, 1985. (b) R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994. (c) G.R. Stephenson, Advanced Asymmetric Synthesis, Chapman and Hall, London, 1996.
4. (a) W.C. Still, A. Mitra, J. Am. Chem. Soc. 100 (1978) 1927.
5. (b) J.S. Sawyer, A. Kucerovy, T.L. Macdonald, G.J. MacGarvey, J. Am. Chem. Soc. 110 (1988) 842.
6. (c) K. Rein, M. Goicoechea-Pappas, T.V. Anklekar, G.C. Hart, G.A. Smith, R.E. Gawley, J. Am. Chem. Soc. 111 (1989) 2211.
7. (d) R.E. Gawley, G.C. Hart, C.J. Bartolotti, J. Org. Chem. 54 (1989) 175.
8. (e) D. Hoppe, F. Hintze, P. Tebben, Angew. Chem. Int. Ed. Engl. 29 (1990) 1422.
9. (f) S.T. Kerrick, P. Beak, J. Am. Chem. Soc. 113 (1991) 9708.
10. (g) W.H. Pearson, A.C. Lindbeck, J. Am. Chem. Soc. 113 (1991) 8546.
11. (a) T. Hayashi, A. Yamamoto, M. Hojo, Y. Ito, J. Chem. Soc. Chem. Commun. (1989) 495.
12. (b) R.C. Petter, C.I. Milberg, Tetrahedron Lett. 30 (1989) 5085.
13. (c) D. Seebach, H. Bossler, H. Gründler, S.-I. Shoda, Helv. Chim. Acta 74 (1991) 197.
14. (d) D. Seebach, A.K. Beck, A. Studer, in: B. Ernst, C. Leumann, (Eds.), Modern Synthetic Methods, vol. 7, VCH, Weinheim, 1995, p. 1.
15. (e) D. Seebach, O. Bezencon, B. Jaun, T. Pietzonka, J.L. Matthews, F.N.M. Kühnle, W.B. Schweizer, Helv. Chim. Acta 79 (1996) 588.
16. D.A. Bors, A. Streitwieser Jr., J. Am. Chem. Soc. 108 (1986) 1397.
17. (a) W. Hollstein, K. Harms, M. Marsch, G. Boche, Angew. Chem. Int. Ed. Engl. 26 (1987) 1287.
18. (b) H.-J. Gais, J. Vollhardt, H. Günther, D. Moskau, H.J. Lindner, S. Braun, J. Am. Chem. Soc. 110 (1988) 978.
19. (c) G. Boche, Angew. Chem. Int. Ed. Engl. 28 (1989) 277.
20. (c) J.F.K. Müller, M. Neuburger, B. Spingler, Angew. Chem. Int. Ed. Engl. 111 (1999) 92.
21. (a) J. Vollhardt, H.-J. Gais, L. Lukas, Angew. Chem. Int. Ed. Engl. 24 (1985) 608.
22. (b) J. Vollhardt, H.-J. Gais, L. Lukas, Angew. Chem. Int. Ed. Engl. 24 (1985) 696.
23. (c) H.-J. Gais, J. Vollhardt, Tetrahedron Lett. 29 (1988) 1529.
24. (a) S. Brenner, M. Bovete, Tetrahedron 31 (1975) 153.
25. (b) E.M. Kaiser, J.D. Petty, P.L.A. Knutson Synthesis (1977) 509.
26. (c) C.J. Kowalsky, M.L. O'Dowd, M.C. Burke, K.W. Fields, J. Am. Chem. Soc. 102 (1980) 5411.
27. (d) H.-H. Vogt, R. Gompper, Chem. Ber. 114 (1981) 2884.
28. (e) D. Seebach, M. Pohmakotr, Tetrahedron 37 (1981) 4047.
29. (f) A. Maerker, M. Theis, Top. Curr. Chem. 138 (1987) 1.
30. (g) C.M. Thomson, Dianion Chemistry in Organic Synthesis, CRC Press, Boca Raton, FL, 1994, p. 1.
31. (h) F. Caturia, C. Nájera, Tetrahedron Lett. 37 (1996) 2833.
32. (i) P. Bonete, C. Nájera, Tetrahedron 52 (1996) 4111.
33. (j) I. Marek, J.-F. Normant, Chem. Rev. 96 (1996) 3241.
34. J.F.K. Müller, M. Neuburger, M. Zehnder, Helv. Chim. Acta 80 (1997) 2182.
35. (a) J.F.K. Müller, R. Batra, B. Spingler, M. Zehnder, Helv. Chim. Acta 79 (1996) 820.
36. (b) J.F.K. Müller, M. Neuburger, M. Zehnder, Acta Crystallogr. Sect. C53 (1997) 419.
37. (a) G.W. Spitznagel, T. Clark, J. Chandrasekhar, P. v. R. Schleyer, J. Comput. Chem. 3 (1982) 363.
38. (b) F. Bernardi, A. Bottoni, A. Venturini, A. Mangini, J. Am. Chem. Soc. 108 (1986) 8171.
39. (a) T. Clark, P. v. R. Schleyer, K.N. Houk, N.G. Rondan, J. Chem. Soc. Chem. Commun. (1981) 579.
40. (b) P. v. R. Schleyer, T. Clark, A.J. Kos, G.W. Spitznagel, G. Rohde, D. Arad, K.N. Houk, N.G. Rondan, J. Am. Chem. Soc. 106 (1984) 6467.
41. (c) G. Boche, J.C.W. Lohrenz, A. Opel, in: A.-M. Sapse, P. v. R. Schleyer (Eds.), Lithium Chemistry, Wiley, New York, 1995, pp. 195-226.
42. (d) A.M. El-Nahas, P. v. R. Schleyer, J. Comput. Chem. 15 (1994) 596.
43. (a) A. Streitwieser Jr., A. Rajca, R.S. McDowell, R. Glaser, J. Am. Chem. Soc. 109 (1987) 4184.
44. (b) S.E. Denmark, C.J. Cramer, J. Org. Chem. 55 (1990) 1806.
45. (c) W. Zarges, M. Marsch, K. Harms, F. Haller, G. Frenking, G. Boche, Chem. Ber. 124 (1991) 861.
46. (d) C.J. Cramer, S.E. Denmark, P.C. Miller, R.L. Dorow, K.A. Swiss, S.R. Wilson, J. Am. Chem. Soc. 116 (1994) 2437.
47. (e) R. Koch, E. Anders, J. Org. Chem. 60 (1995) 5861.
48. (f) M. Kranz, S.E. Denmark, J. Org. Chem. 60 (1995) 5867.
49. (g) M. Kranz, S.E. Denmark, K.A. Swiss, S.R. Wilson, J. Org. Chem. 61 (1996) 8551.
50. (a) S. Wolfe, A. Rauk, I.G. Csizmadia, J. Am. Chem. Soc. 91 (1969) 1567.
51. (b) S. Wolfe, A. Rauk, L.M. Tel, I.G. Csizmadia, J. Chem. Soc. Chem. Commun. (1970) 96.
52. (c) A. Streitwieser Jr., J.E. Williams Jr., J. Am. Chem. Soc. 97 (1975) 191.
53. (d) S. Wolfe, A. Stolow, L.A. La John, Tetrahedron Lett. 24 (1983) 4071.
54. (e) S. Wolfe, L.A. La John, D.E. Weaver, Tetrahedron Lett. 25 (1984) 2863.
55. (f) T. Clark, in: C. Chatgiliaoglu, K.-D. Asmus (Eds.), Sulfur Centered Reactive Intermediates In Chemistry and Biology, NATO ASI Series A, Life Sciences, vol. 197, Plenum Press, New York, 1990, p. 13.
56. (g) R. Koch, E. Anders, J. Org. Chem. 59 (1994) 4529.
57. (a) P. Hohenberg, W. Kohn, Phys. Rev. 136 (1964) B 864.
58. (b) W. Kohn, L. Sham, J. Phys. Rev. 140 (1965) A1133.
59. (c) J.C. Slater, Quantum Theory of Molecular and Solids, vol. 4: The Self-Consistent Field of Molecular and Solids, McGraw-Hill, New York, 1974.
60. (d) A.D. Becke, Phys. Rev. A 38 (1988) 3098.
61. (e) A.D. Becke, J. Chem. Phys. 98 (1993) 1372.
62. (f) J.P. Perdew, Y. Wang, Phys. Rev. B 45 (1992) 13244.
63. (g) R.G. Parr, Y. Wang, Density-Functional Theory of Atoms and Molecules, Oxford University Press, Oxford, 1989.
64. (a) A.E. Reed, F. Weinhold, J. Chem. Phys. 78 (1983) 4066.
65. (b) A.E. Reed, F. Weinhold, R.B. Weinstock, J. Chem. Phys. 83 (1985) 735.
66. (c) A.E. Reed, F. Weinhold, J. Chem. Phys. (1985) 83, 1736.
67. (d) A.E. Reed, P. v. R. Schleyer, J. Am. Chem. Soc. 109 (1987) 7362.
68. (e) A.E. Reed, L.A. Curtiss, F. Weinhold, Chem. Rev. 88 (1988) 899.
69. M.J. Frisch, G.W. Trucks, H.B. Schlegel, P.M.W. Gill, B.G. Johnson, M.A. Robb, J.R. Cheeseman, T. Keith, G.A. Petersson, J.A. Montgomery, K. Raghavachari, M.A. Al-Laham, V.G. Zakrzewski, J.V. Ortiz, J.B. Foresman, J. Cioslowski, B.B. Stefanov, A. Nanayakkara, M. Challacombe, C.Y. Peng, P.Y. Ayala, W. Chen, M.W. Wong, J.L. Andres, E.S. Replogle, R. Gomperts, R.L. Martin, D.J. Fox, J.S. Binkley, D.J. Defrees, J. Baker, J.P. Stewart, M. Head-Gordon, C. Gonzalez, J.A. Pople, Gaussian 94, Revision B.2, Gaussian, Inc., Pittsburgh, PA, 1995.
70. W.J. Hehre, L. Radom, P. v. R. Schleyer, J.A. Pople, Ab Initio Molecular Orbital Theory, Wiley Intersience, New York, 1986.
71. (a) C. Møller, M.S. Plesset, Phys. Rev. 46 (1934) 618.
72. (b) J.S. Binkley, J.A. Pople, Int. J. Quant. Chem. 9 (1975) 229.
73. (a) J.W. Ochterski, G.A. Petersson, K.B. Wiberg, J. Am. Chem. Soc. 117 (1995) 11299.
74. (b) J.W. Ochterski, G.A. Petersson, J. Montgomery Jr., J. Chem. Phys. 104 (1996) 2598.
75. H.-J. Gais, D. Lenz, G. Raabe, Tetrahedron Lett. 36 (1995) 7437.
76. (a) J.B. Collins, P. v. R. Schleyer, J.S. Binkley, J.A. Pople, J. Chem. Phys. 64 (1976) 5142.
77. (b) J. Chandrasekhar, J. Andrade, P. v. R. Schleyer, J. Am. Chem. Soc. 103 (1981) 5609.
78. (c) M.M. Francl, W.J. Pietro, W.J. Hehre, J.S. Binkley, M.S. Gordon, D.J. DeFrees, J.A. Pople, J. Chem. Phys. 77 (1982) 3654.
79. U. Salzner, P. v. R. Schleyer, J. Am. Chem. Soc. 115 (1993) 10231.
80. G. Raabe, H.-J. Gais, J. Fleischhauer, J. Am. Chem. Soc. 118 (1996) 4622.