Reactivity of ether-and amine-complexed dimers and tetramers of alkyllithiums towards triphenylmethane

Chemistry - A European Journal

Volumn 6, Issue 2, 2000, Pages 225-236

  Moene, Willem ^a   Vos, Marcel ^a   Schakel, Marius ^a   De Kanter, Frans J J ^a   Schmitz, Robert F ^a   Klumpp, Gerhard W ^a  

^a VU UNIVERSITY AMSTERDAM   (Netherlands)

Author keywords

Aggregation; Kinetics; Lithiation; Precomplexes; Triphenylmethane

Indexed keywords

DIMER; ETHER DERIVATIVE; LITHIUM DERIVATIVE; TETRAMER; TRIPHENYLMETHANE;

ARTICLE; CHEMICAL REACTION; COMPLEX FORMATION; KINETICS; REACTION ANALYSIS; SPECTROSCOPY; STRUCTURE ANALYSIS; X RAY ANALYSIS;

EID: 0033959690     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3765(20000117)6:2<225::aid-chem225>3.3.co;2-t     Document Type: Article

References (77)

1. a) M. Schlosser, Polare Organometalle, Springer, Berlin, 1973;
2. b) B. J. Wakefield, The Chemistry of Organolithium Compounds, Pergamon Press, Oxford, 1974;
3. c) J. C. Stowell, Carbanions in Organic Synthesis, Wiley, New York, 1979;
4. d) B. J. Wakefield in Comprehensive Organic Chemistry, Vol. 3 (Eds.: D. H. R. Barton, W. D. Ollis), Pergamon Press, Oxford, 1979, p. 943;
5. e) B. J. Wakefield in Comprehensive Organometallic Chemistry, Vol. 7 (Eds.: G. Wilkinson, F. G. A. Stone, E. W. Abel), Pergamon Press, Oxford, 1982, p. 2;
6. f) R. B. Bates, C. A. Ogle, Carbanion Chemistry, Springer, Berlin, 1983;
7. g) L. Brandsma, H. Verkruijsse, Preparative Polar Organometallic Chemistry-1, Springer, Berlin, 1987.
8. a) K. C. Williams, T. L. Brown, J. Am. Chem. Soc. 1966, 88, 4134-4140;
9. b) H. L. Lewis, T. L. Brown, J. Am. Chem. Soc. 1970, 92, 4664-4670;
10. c) J. Heinzer, J. F. M. Oth, D. Seebach, Helv. Chim. Acta 1985, 68, 1848-1862;
11. d) T. F. Bates, M. T. Clarke, R. D. Thomas, J. Am. Chem. Soc. 1988, 110, 5109-5112;
12. e) W. Bauer, W. R. Winchester, P. von R. Schleyer, Organometallics 1987, 6, 2371-2379;
13. f) G. Fraenkel, A. Chow, W. R. Winchester, J. Am. Chem. Soc. 1990, 112, 6190-6198, and references 1-12 therein.
14. [4]) could be determined only in few cases: a) P. West, R. Waak, P. I. Purmont, J. Am. Chem. Soc. 1970, 92, 840-845;
15. b) T. Holm, Acta Chem. Scand. B 1978, 32, 162-166;
16. c) J. F. McGarrity, C. A. Ogle, Z. Brich, H.-R. Loosli, J. Am. Chem. Soc. 1985, 107, 1810-1815;
17. d) H. J. Reich, D. P. Green, N. H. Phillips, J. Am. Chem. Soc. 1991, 113, 1414-1416; see also ref. [2d].
18. a) W. H. Glaze, C. H. Freeman, J. Am. Chem. Soc. 1969, 91, 7198-7199;
19. b) M. Vos, F. J. J. de Kanter, M. Schakel, N. J. R. van Eikema Hommes, G. W. Klumpp, J. Am. Chem. Soc. 1987, 109, 2187-2188;
20. c) B. O. T. Kammermeier, G. W. Klumpp, K. Kolthof, M. Vos, Tetrahedron Lett. 1991, 32, 3111-3114.
21. Influence of complexation and aggregation on chemoselectivity: a) H. Luitjes, M. Schakel, R. F. Schmitz, G. W. Klumpp, Angew. Chem. 1995, 107, 2324-2325; Angew. Chem. Int. Ed. Engl. 1995, 34, 2152-2153;
22. Influence of complexation and aggregation on chemoselectivity: a) H. Luitjes, M. Schakel, R. F. Schmitz, G. W. Klumpp, Angew. Chem. 1995, 107, 2324-2325; Angew. Chem. Int. Ed. Engl. 1995, 34, 2152-2153;
23. b) H. Luitjes, M. Schakel, M. P. Aarnts, R. F. Schmitz, F. J. J. de Kanter, G. W. Klumpp, Tetrahedron 1997, 53, 9977-9988.
24. Influence of complexation and aggregation on stereoselectivity: G. Cainelli, D. Giacomini, M. Walzl, Angew. Chem. 1995, 107, 2336-2338; Angew. Chem. Int. Ed. Engl. 1995, 34, 2150-2152.
25. Influence of complexation and aggregation on stereoselectivity: G. Cainelli, D. Giacomini, M. Walzl, Angew. Chem. 1995, 107, 2336-2338; Angew. Chem. Int. Ed. Engl. 1995, 34, 2150-2152.
26. a) 1: G. W. Klumpp, M. Vos, F. J. J. de Kanter, C. Slob, H. Krabbendam, A. L. Spek, J. Am. Chem. Soc. 1985, 107, 8292-8294;
27. b) 2: G. W. Klumpp, P. J. A. Geurink, N. J. R. van Eikema Hommes, F. J. J. de Kanter, M. Vos, A. L. Spek, Recl. Trav. Chim. Pays-Bas 1986, 105, 398-403;
28. c) 6: W. Moene, M. Vos, F. J. J. de Kanter, G. W. Klumpp, A. L. Spek, J. Am. Chem. Soc. 1989, 111, 3463-3465;
29. d) 8: see ref. [4b];
30. e) 9: W. Moene, M. Schakel, G. J. M. Hoogland, F. J. J. de Kanter, G. W. Klumpp, Tetrahedron Lett. 1990, 31, 2641-2642.
31. W. Bauer, T. Clark, P. von R. Schleyer, J. Am. Chem. Soc. 1987, 109, 970-977.
32. P. West, R. Waak, J. I. Purmort, J. Organomet. Chem. 1969, 19, 267-277.
33. H. Luitjes, F. J. J. de Kanter, M. Schakel, R. F. Schmitz, G. W. Klumpp, J. Am. Chem. Soc. 1995, 117, 4179-4180.
34. [7a,b]
35. T. L. Brown, Adv. Organomet. Chem. 1965, 3, 365-395; T. L. Brown, J. Organomet. Chem. 1966, 5, 191-194.
36. T. L. Brown, Adv. Organomet. Chem. 1965, 3, 365-395; T. L. Brown, J. Organomet. Chem. 1966, 5, 191-194.
37. m.
38. α-Lithiation of tertiary amines: D. J. Gallagher, P. Beak, J. Org. Chem. 1995, 60 7092-7093, and references therein; addition to ketones: D. Lozach, G. Molle, P. Bauer, J. E. Dubois, Tetrahedron Lett. 1983, 24, 4213-4216; addition to epoxide: S. Harder, J. Boersma, L. Brandsma, J. A. Kanters, A. J. M. Duisenberg, J. H. van Lenthe, Organometallics 1990, 9, 511-516.
39. α-Lithiation of tertiary amines: D. J. Gallagher, P. Beak, J. Org. Chem. 1995, 60 7092-7093, and references therein; addition to ketones: D. Lozach, G. Molle, P. Bauer, J. E. Dubois, Tetrahedron Lett. 1983, 24, 4213-4216; addition to epoxide: S. Harder, J. Boersma, L. Brandsma, J. A. Kanters, A. J. M. Duisenberg, J. H. van Lenthe, Organometallics 1990, 9, 511-516.
40. α-Lithiation of tertiary amines: D. J. Gallagher, P. Beak, J. Org. Chem. 1995, 60 7092-7093, and references therein; addition to ketones: D. Lozach, G. Molle, P. Bauer, J. E. Dubois, Tetrahedron Lett. 1983, 24, 4213-4216; addition to epoxide: S. Harder, J. Boersma, L. Brandsma, J. A. Kanters, A. J. M. Duisenberg, J. H. van Lenthe, Organometallics 1990, 9, 511-516.
41. f between 0.5 and 1 also result if both species of Equation (3a) (mechanism 2) enter into reaction directly.
42. P. von R. Schleyer, T. Clark, A. J. Kos, G. W. Spitznagel, C. Rohde, D. Arat, K. N. Houk, N. G. Rondan, J. Am. Chem. Soc. 1984, 106, 6467-6475.
43. P. Magnus, Aldrichimica Acta 1980, 13, 43-51.
44. A. Van Vulpen, J. Coops, Recl. Trav. Chim. Pays-Bas 1966, 85, 203-215 ; H. C. Holtkamp, C. Blomberg, F. Bickelhaupt, J. Organomet. Chem. 1969, 19, 279-285 .
45. A. Van Vulpen, J. Coops, Recl. Trav. Chim. Pays-Bas 1966, 85, 203-215 ; H. C. Holtkamp, C. Blomberg, F. Bickelhaupt, J. Organomet. Chem. 1969, 19, 279-285 .
46. H. Günther, D. Moskau, P. Bast, D. Schmalz, Angew. Chem. 1987, 99, 1242-1250; Angew. Chem. Int. Ed. Engl. 1987, 26, 1212-1220; W. Bauer, W. R. Winchester, P. von R. Schleyer, Organometallics 1987, 6, 2371-2379.
47. H. Günther, D. Moskau, P. Bast, D. Schmalz, Angew. Chem. 1987, 99, 1242-1250; Angew. Chem. Int. Ed. Engl. 1987, 26, 1212-1220; W. Bauer, W. R. Winchester, P. von R. Schleyer, Organometallics 1987, 6, 2371-2379.
48. H. Günther, D. Moskau, P. Bast, D. Schmalz, Angew. Chem. 1987, 99, 1242-1250; Angew. Chem. Int. Ed. Engl. 1987, 26, 1212-1220; W. Bauer, W. R. Winchester, P. von R. Schleyer, Organometallics 1987, 6, 2371-2379.
49. T. Clark, P. von R. Schleyer, K. N. Houk, N. G. Rondan, J. Chem. Soc. Chem. Commun. 1981, 579-581.
50. Compare with D. J. Peterson, J. Am. Chem. Soc. 1971, 93, 4027-4031. Formation of ethylene could take place in a dimer of 15; occurrence of methylene is improbable.
51. M. Vos, K. Kolthof, A. L. Spek, unpublished results.
52. 2 complexed to lithium by TPMLi (G. Köbrich, A. Baumann, Angew. Chem. 1973, 85, 916-918;
53. [7e] and 5 (see Experimental Section).
54. 4, see refs. [2c] and [2f], respectively.
55. 2 with LB:Li = 1, that is, it lacks two such bonds, must be higher
56. -1.
57. m interaction: S. Bywater, D. J. Worsfold, J. Organomet. Chem. 1967, 10, 1-6;
58. J. R. Urchin, P. J. Reed, J. Organomet. Chem. 1968, 15, 1-5;
59. M. V. Sergutin, N. G. Antonov, V. N. Zgonnik, K. K. Kalninsh, J. Organomet. Chem. 1978, 145, 265-267;
60. 6 · 2 benzene (R. Zerger, W. Rhine, G. Stucky, J. Am. Chem. Soc. 1974, 96, 6048-6055);
61. b) Calculational evidence: N. J. R. van Eikema Hommes, P. von R. Schleyer, Tetrahedron 1994, 50, 5903-5916);
62. c) Our preference for benzene over an alkane solvent at the outset of this work was based on the higher solubilities of TPMH and TPMLi in the former.
63. 2) could be formed with 1,1-diphenylethene. In 1982, we found that in the addition to 1,1-diphenylethene, 3-lithio-1-methoxybutane has an effective reaction order of 0.75 (P. J. A. Geurink, Dissertation, Vrije Universiteit, Amsterdam, 1982).
64. 2) could be formed with 1,1-diphenylethene. In 1982, we found that in the addition to 1,1-diphenylethene, 3-lithio-1-methoxybutane has an effective reaction order of 0.75 (P. J. A. Geurink, Dissertation, Vrije Universiteit, Amsterdam, 1982).
65. R. F. Schmitz, M. Schakel, M. Vos, G. W. Klumpp, Chem. Commun. 1998, 1099-1100.
66. E. Weiss, Angew. Chem. 1993, 105, 1565-1587; Angew. Chem. Int. Ed. Engl. 1993, 32, 1501-1523.
67. E. Weiss, Angew. Chem. 1993, 105, 1565-1587; Angew. Chem. Int. Ed. Engl. 1993, 32, 1501-1523.
68. [9]
69. Similar suggestions have been made: E. Kaufmann; P. von R. Schleyer, K. N. Houk, Y.-D. Wu, J. Am. Chem. Soc. 1985, 107, 5560-5562; D. R. Hay, Z Song, S. G. Smith, P. Beak, J. Am. Chem. Soc. 1988, 110, 8145-8153.
70. Similar suggestions have been made: E. Kaufmann; P. von R. Schleyer, K. N. Houk, Y.-D. Wu, J. Am. Chem. Soc. 1985, 107, 5560-5562; D. R. Hay, Z Song, S. G. Smith, P. Beak, J. Am. Chem. Soc. 1988, 110, 8145-8153.
71. D. Seebach, R. Hässig, J. Gabriel, Helv. Chim. Acta 1983, 66, 308-337.
72. 4 in cyclohexane, a marked rate acceleration evidenced its involvement in a transition state (M. Y. Darensbourg, B. Y. Kimura, G. E. Hartwell, T. L. Brown, J. Am. Chem. Soc. 1970, 92, 1236-1242).
73. H. Gilman, F. K. Cartledge, J. Organomet. Chem. 1964, 2, 447-454.
74. R. F. Brown, N. M. van Gulick, J. Am. Chem. Soc. 1955, 77, 1089-1092.
75. S. W. Pelletier, J. E. Franz, J. Org. Chem. 1952, 17, 855-859.
76. C. Mannich, Arch. Pharm. 1917, 255, 261-276.
77. F. J. Blicke, F. J. McCarthy, J. Org. Chem. 1959, 24, 1376-1379.