The reactivity of tetramesityldisilene with epoxides: Dependence of product distributions on steric and structural characteristics of the epoxide

Journal of Organometallic Chemistry

Volumn 521, Issue 1-2, 1996, Pages 363-375

  Mangette, John E ^a   Powell, Douglas R ^a   Firman, Timothy K ^a   West, Robert ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

Crystal structure; Cycloaddition; Disilene; Epoxide; Group 14; Silyl enol ether; Steric effects

Indexed keywords

EID: 0030598769     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0022-328X(95)06069-9     Document Type: Article

References (68)

1. [1] J.E. Mangette, D.R. Powell and R. West, J. Chem. Soc., Chem. Commun., (1993) 1348.
2. [2] J.E. Mangette, D.R. Powell and R. West, Organometallics, 13 (1994) 4097; J.E. Mangette, D.R. Powell, J.C. Calabrese and R. West, Organometallics, 14 (1995) 4064.
3. [2] J.E. Mangette, D.R. Powell and R. West, Organometallics, 13 (1994) 4097; J.E. Mangette, D.R. Powell, J.C. Calabrese and R. West, Organometallics, 14 (1995) 4064.
4. [3] H.B. Yokelson, A.J. Millevolte, G.R. Gillette and R. West, J. Am. Chem. Soc., 109 (1987) 6865.
5. [4] Y. Pocker, in P. DeMayo (ed.), Molecular Rearrangements, Wiley, New York, 1963, p. 15; M. Bartók and K.L. Láng, in A. Hassner (ed.), Heterocyclic Compounds, Vol. 42, Wiley, New York, 1985, Part 3, p. 65.
6. [4] Y. Pocker, in P. DeMayo (ed.), Molecular Rearrangements, Wiley, New York, 1963, p. 15; M. Bartók and K.L. Láng, in A. Hassner (ed.), Heterocyclic Compounds, Vol. 42, Wiley, New York, 1985, Part 3, p. 65.
7. 1H NMR integration was applicable to the reactions of 1 with the phenyl-substituted epoxides, since the corresponding alkenes are higher boiling than cyclohexene.
8. [6] For details on the synthesis and characterization of 7f, see Ref. [2]. For previous work on additions of carbonyl compounds to 1, see A.D. Fanta, D.J. DeYoung, J. Belzner and R. West, Organometallics, 10 (1991) 3466; A.D. Fanta, J. Belzner, D.R. Powell and R. West, Organometallics, 12 (1993) 2177.
9. [6] For details on the synthesis and characterization of 7f, see Ref. [2]. For previous work on additions of carbonyl compounds to 1, see A.D. Fanta, D.J. DeYoung, J. Belzner and R. West, Organometallics, 10 (1991) 3466; A.D. Fanta, J. Belzner, D.R. Powell and R. West, Organometallics, 12 (1993) 2177.
10. [7] F.B. Padley, in G.B. Marini-Bettòlo (ed.), Thin Layer Chromatography, Elsevier, Amsterdam, 1964, p. 90; G.M. Nano and A. Martelli, J. Chromatogr., 21 (1966) 349.
11. [7] F.B. Padley, in G.B. Marini-Bettòlo (ed.), Thin Layer Chromatography, Elsevier, Amsterdam, 1964, p. 90; G.M. Nano and A. Martelli, J. Chromatogr., 21 (1966) 349.
12. [8] E.A. Williams, in S. Patai and Z. Rappoport (eds.), The Chemistry of Organosilicon Compounds, Wiley, New York, 1989, Chapter 8, pp. 547-549; H. Marsmann, in P. Diehl, E. Fluck and R. Kosfeld (eds.), NMR Basic Principles and Progress, Vol. 17, Springer, Berlin, 1981, pp. 112-135.
13. [8] E.A. Williams, in S. Patai and Z. Rappoport (eds.), The Chemistry of Organosilicon Compounds, Wiley, New York, 1989, Chapter 8, pp. 547-549; H. Marsmann, in P. Diehl, E. Fluck and R. Kosfeld (eds.), NMR Basic Principles and Progress, Vol. 17, Springer, Berlin, 1981, pp. 112-135.
14. [9] (a) P. Fischer, in S. Patai (ed.), The Chemistry of Ethers, Crown Ethers, Hydroxyl Groups and Their Sulfur Analogues Suppl. E, Wiley, New York, 1980, Part 2, Chapter 17, pp. 769-771. A.C. Rojas, J.K. Crandall, J. Org. Chem., 40 (1975) 2225; E. Taskinen, Tetrahedron, 34 (1978) 425; M.P. Strobel, C.G. Andrieu, D. Paquer, M. Vazeux and C.C. Pham, Nouv. J. Chim., 4 (1980) 101; E. Friedrich, H.-O. Kalinowski and W. Lutz, Tetrahedron, 36 (1980) 1051.
15. [9] (a) P. Fischer, in S. Patai (ed.), The Chemistry of Ethers, Crown Ethers, Hydroxyl Groups and Their Sulfur Analogues Suppl. E, Wiley, New York, 1980, Part 2, Chapter 17, pp. 769-771. A.C. Rojas, J.K. Crandall, J. Org. Chem., 40 (1975) 2225; E. Taskinen, Tetrahedron, 34 (1978) 425; M.P. Strobel, C.G. Andrieu, D. Paquer, M. Vazeux and C.C. Pham, Nouv. J. Chim., 4 (1980) 101; E. Friedrich, H.-O. Kalinowski and W. Lutz, Tetrahedron, 36 (1980) 1051.
16. [9] (a) P. Fischer, in S. Patai (ed.), The Chemistry of Ethers, Crown Ethers, Hydroxyl Groups and Their Sulfur Analogues Suppl. E, Wiley, New York, 1980, Part 2, Chapter 17, pp. 769-771. A.C. Rojas, J.K. Crandall, J. Org. Chem., 40 (1975) 2225; E. Taskinen, Tetrahedron, 34 (1978) 425; M.P. Strobel, C.G. Andrieu, D. Paquer, M. Vazeux and C.C. Pham, Nouv. J. Chim., 4 (1980) 101; E. Friedrich, H.-O. Kalinowski and W. Lutz, Tetrahedron, 36 (1980) 1051.
17. [9] (a) P. Fischer, in S. Patai (ed.), The Chemistry of Ethers, Crown Ethers, Hydroxyl Groups and Their Sulfur Analogues Suppl. E, Wiley, New York, 1980, Part 2, Chapter 17, pp. 769-771. A.C. Rojas, J.K. Crandall, J. Org. Chem., 40 (1975) 2225; E. Taskinen, Tetrahedron, 34 (1978) 425; M.P. Strobel, C.G. Andrieu, D. Paquer, M. Vazeux and C.C. Pham, Nouv. J. Chim., 4 (1980) 101; E. Friedrich, H.-O. Kalinowski and W. Lutz, Tetrahedron, 36 (1980) 1051.
18. [9] (a) P. Fischer, in S. Patai (ed.), The Chemistry of Ethers, Crown Ethers, Hydroxyl Groups and Their Sulfur Analogues Suppl. E, Wiley, New York, 1980, Part 2, Chapter 17, pp. 769-771. A.C. Rojas, J.K. Crandall, J. Org. Chem., 40 (1975) 2225; E. Taskinen, Tetrahedron, 34 (1978) 425; M.P. Strobel, C.G. Andrieu, D. Paquer, M. Vazeux and C.C. Pham, Nouv. J. Chim., 4 (1980) 101; E. Friedrich, H.-O. Kalinowski and W. Lutz, Tetrahedron, 36 (1980) 1051.
19. [10] E.A. Williams, S. Patai and Z. Rappoport (eds.), The Chemistry of Organosilicon Compounds, Wiley, New York, 1989, Chapter 8, pp. 523-527.
20. [11] H.R. Warner and W.E.M. Lands, J. Am. Chem. Soc., 85 (1963) 60; H.O. House, L.J. Czuba, M. Gall and H.D. Olmstead, J. Org. Chem., 34 (1969) 2324; E. Taskinen and P. Liukas, Acta Chem. Scand., B28 (1974) 114.
21. [11] H.R. Warner and W.E.M. Lands, J. Am. Chem. Soc., 85 (1963) 60; H.O. House, L.J. Czuba, M. Gall and H.D. Olmstead, J. Org. Chem., 34 (1969) 2324; E. Taskinen and P. Liukas, Acta Chem. Scand., B28 (1974) 114.
22. [11] H.R. Warner and W.E.M. Lands, J. Am. Chem. Soc., 85 (1963) 60; H.O. House, L.J. Czuba, M. Gall and H.D. Olmstead, J. Org. Chem., 34 (1969) 2324; E. Taskinen and P. Liukas, Acta Chem. Scand., B28 (1974) 114.
23. [12] L.M. Jackman and S. Sternhell, Applications of Nuclear Magnetic Resonance in Organic Chemistry, Pergamon Press, New York, 1969, pp. 301-302.
24. 4 unit of 6g sits on a two-fold crystallographic axis with the oxygen and cyclohexyl ring disordered 1:1.
25. [14] It is assumed that E5/Z5 isomerization does not occur under the reaction conditions. This assumption is validated by detailed control experiments from the stilbene oxide study, which showed that the stilbene derivatives of 5 were configurationally stable under the reaction conditions [2], and by the observation that phenyl-substituted alkenes undergo isomerization more readily than alkyl-substituted alkenes. H.-O. Kalinowski and H. Kessler, Top. Stereochem., 7 (1973) 295.
26. [15] F.R. Jensen and C.H. Bushweller, Adv. Alicyclic Chem., 3 (1971) 139; J.A. Hirsch, Top. Stereochem., 1 (1967) 199; E.L. Eliel and M. Manoharan, J. Org. Chem., 46 (1981) 1959.
27. [15] F.R. Jensen and C.H. Bushweller, Adv. Alicyclic Chem., 3 (1971) 139; J.A. Hirsch, Top. Stereochem., 1 (1967) 199; E.L. Eliel and M. Manoharan, J. Org. Chem., 46 (1981) 1959.
28. [15] F.R. Jensen and C.H. Bushweller, Adv. Alicyclic Chem., 3 (1971) 139; J.A. Hirsch, Top. Stereochem., 1 (1967) 199; E.L. Eliel and M. Manoharan, J. Org. Chem., 46 (1981) 1959.
29. [16] P.B.D. De La Mare and B.E. Swedlund, in S. Patai (ed.), The Chemistry of the Carbon-Halogen Bond, Wiley, New York, 1973, Part 1, Chapter 7, pp. 417-421; P.D. Bartlett and L.J. Rosen, J. Am. Chem. Soc., 64 (1942) 543; I. Dostrovsky, E.D. Hughes and C.K. Ingold, J. Chem. Soc., (1946) 173.
30. [16] P.B.D. De La Mare and B.E. Swedlund, in S. Patai (ed.), The Chemistry of the Carbon-Halogen Bond, Wiley, New York, 1973, Part 1, Chapter 7, pp. 417-421; P.D. Bartlett and L.J. Rosen, J. Am. Chem. Soc., 64 (1942) 543; I. Dostrovsky, E.D. Hughes and C.K. Ingold, J. Chem. Soc., (1946) 173.
31. [16] P.B.D. De La Mare and B.E. Swedlund, in S. Patai (ed.), The Chemistry of the Carbon-Halogen Bond, Wiley, New York, 1973, Part 1, Chapter 7, pp. 417-421; P.D. Bartlett and L.J. Rosen, J. Am. Chem. Soc., 64 (1942) 543; I. Dostrovsky, E.D. Hughes and C.K. Ingold, J. Chem. Soc., (1946) 173.
32. [17] H.C. Brown, R.S. Fletcher and R.B. Johannesen, J. Am. Chem. Soc., 73 (1951) 212; H.C. Brown and M. Borkowski, J. Am. Chem. Soc., 74 (1952) 1894; K. Ranganayakulu, M. Vasumathi Devi, R. Balaji Rao and K. Rajeswari, Can. J. Chem., 58 (1980) 1484; H.-J. Schneider and F. Thomas, J. Am. Chem. Soc., 102 (1980) 1424.
33. [17] H.C. Brown, R.S. Fletcher and R.B. Johannesen, J. Am. Chem. Soc., 73 (1951) 212; H.C. Brown and M. Borkowski, J. Am. Chem. Soc., 74 (1952) 1894; K. Ranganayakulu, M. Vasumathi Devi, R. Balaji Rao and K. Rajeswari, Can. J. Chem., 58 (1980) 1484; H.-J. Schneider and F. Thomas, J. Am. Chem. Soc., 102 (1980) 1424.
34. [17] H.C. Brown, R.S. Fletcher and R.B. Johannesen, J. Am. Chem. Soc., 73 (1951) 212; H.C. Brown and M. Borkowski, J. Am. Chem. Soc., 74 (1952) 1894; K. Ranganayakulu, M. Vasumathi Devi, R. Balaji Rao and K. Rajeswari, Can. J. Chem., 58 (1980) 1484; H.-J. Schneider and F. Thomas, J. Am. Chem. Soc., 102 (1980) 1424.
35. [17] H.C. Brown, R.S. Fletcher and R.B. Johannesen, J. Am. Chem. Soc., 73 (1951) 212; H.C. Brown and M. Borkowski, J. Am. Chem. Soc., 74 (1952) 1894; K. Ranganayakulu, M. Vasumathi Devi, R. Balaji Rao and K. Rajeswari, Can. J. Chem., 58 (1980) 1484; H.-J. Schneider and F. Thomas, J. Am. Chem. Soc., 102 (1980) 1424.
36. [18] B.N. Blackett, J.M. Coxon, M.P. Hartshorn and K.E. Richards, Tetrahedron, 25 (1969) 4999; B.N. Blackett, J.M. Coxon, M.P. Hartshorn and K.E. Richards, Australian J. Chem., 23 (1970) 2077; B.N. Blackett, J.M. Coxon, M.P. Hartshorn and K.E. Richards, J. Am. Chem. Soc., 92 (1970) 2574; J.M. Coxon and C.-E. Lim, Australian J. Chem., 30 (1977) 1137; J.W. Blunt, J.M. Coxon, C.-E. Lim and H.A. Schuyt, Australian J. Chem., 36 (1983) 97; J.M. Coxon and M.P. Hartshorn, Tetrahedron Lett., 28 (1987) 1333; J.M. Coxon and D.Q. McDonald, Tetrahedron Lett., 29 (1988) 2575; V.C. Ukachukwu and D.L. Whalen, Tetrahedron Lett., 29 (1988) 293; V.C. Ukachukwu, J.J. Blumenstein and D.L. Whalen, J. Am. Chem. Soc., 108 (1986) 5039; Y. Pocker, B.P. Ronald and K.W. Anderson, J. Am. Chem. Soc., 110 (1988) 6492; K. Maruoka, T. Ooi and H. Yamamoto, Tetrahedron, 48 (1992) 3303.
37. [18] B.N. Blackett, J.M. Coxon, M.P. Hartshorn and K.E. Richards, Tetrahedron, 25 (1969) 4999; B.N. Blackett, J.M. Coxon, M.P. Hartshorn and K.E. Richards, Australian J. Chem., 23 (1970) 2077; B.N. Blackett, J.M. Coxon, M.P. Hartshorn and K.E. Richards, J. Am. Chem. Soc., 92 (1970) 2574; J.M. Coxon and C.-E. Lim, Australian J. Chem., 30 (1977) 1137; J.W. Blunt, J.M. Coxon, C.-E. Lim and H.A. Schuyt, Australian J. Chem., 36 (1983) 97; J.M. Coxon and M.P. Hartshorn, Tetrahedron Lett., 28 (1987) 1333; J.M. Coxon and D.Q. McDonald, Tetrahedron Lett., 29 (1988) 2575; V.C. Ukachukwu and D.L. Whalen, Tetrahedron Lett., 29 (1988) 293; V.C. Ukachukwu, J.J. Blumenstein and D.L. Whalen, J. Am. Chem. Soc., 108 (1986) 5039; Y. Pocker, B.P. Ronald and K.W. Anderson, J. Am. Chem. Soc., 110 (1988) 6492; K. Maruoka, T. Ooi and H. Yamamoto, Tetrahedron, 48 (1992) 3303.
38. [18] B.N. Blackett, J.M. Coxon, M.P. Hartshorn and K.E. Richards, Tetrahedron, 25 (1969) 4999; B.N. Blackett, J.M. Coxon, M.P. Hartshorn and K.E. Richards, Australian J. Chem., 23 (1970) 2077; B.N. Blackett, J.M. Coxon, M.P. Hartshorn and K.E. Richards, J. Am. Chem. Soc., 92 (1970) 2574; J.M. Coxon and C.-E. Lim, Australian J. Chem., 30 (1977) 1137; J.W. Blunt, J.M. Coxon, C.-E. Lim and H.A. Schuyt, Australian J. Chem., 36 (1983) 97; J.M. Coxon and M.P. Hartshorn, Tetrahedron Lett., 28 (1987) 1333; J.M. Coxon and D.Q. McDonald, Tetrahedron Lett., 29 (1988) 2575; V.C. Ukachukwu and D.L. Whalen, Tetrahedron Lett., 29 (1988) 293; V.C. Ukachukwu, J.J. Blumenstein and D.L. Whalen, J. Am. Chem. Soc., 108 (1986) 5039; Y. Pocker, B.P. Ronald and K.W. Anderson, J. Am. Chem. Soc., 110 (1988) 6492; K. Maruoka, T. Ooi and H. Yamamoto, Tetrahedron, 48 (1992) 3303.
39. [18] B.N. Blackett, J.M. Coxon, M.P. Hartshorn and K.E. Richards, Tetrahedron, 25 (1969) 4999; B.N. Blackett, J.M. Coxon, M.P. Hartshorn and K.E. Richards, Australian J. Chem., 23 (1970) 2077; B.N. Blackett, J.M. Coxon, M.P. Hartshorn and K.E. Richards, J. Am. Chem. Soc., 92 (1970) 2574; J.M. Coxon and C.-E. Lim, Australian J. Chem., 30 (1977) 1137; J.W. Blunt, J.M. Coxon, C.-E. Lim and H.A. Schuyt, Australian J. Chem., 36 (1983) 97; J.M. Coxon and M.P. Hartshorn, Tetrahedron Lett., 28 (1987) 1333; J.M. Coxon and D.Q. McDonald, Tetrahedron Lett., 29 (1988) 2575; V.C. Ukachukwu and D.L. Whalen, Tetrahedron Lett., 29 (1988) 293; V.C. Ukachukwu, J.J. Blumenstein and D.L. Whalen, J. Am. Chem. Soc., 108 (1986) 5039; Y. Pocker, B.P. Ronald and K.W. Anderson, J. Am. Chem. Soc., 110 (1988) 6492; K. Maruoka, T. Ooi and H. Yamamoto, Tetrahedron, 48 (1992) 3303.
40. [18] B.N. Blackett, J.M. Coxon, M.P. Hartshorn and K.E. Richards, Tetrahedron, 25 (1969) 4999; B.N. Blackett, J.M. Coxon, M.P. Hartshorn and K.E. Richards, Australian J. Chem., 23 (1970) 2077; B.N. Blackett, J.M. Coxon, M.P. Hartshorn and K.E. Richards, J. Am. Chem. Soc., 92 (1970) 2574; J.M. Coxon and C.-E. Lim, Australian J. Chem., 30 (1977) 1137; J.W. Blunt, J.M. Coxon, C.-E. Lim and H.A. Schuyt, Australian J. Chem., 36 (1983) 97; J.M. Coxon and M.P. Hartshorn, Tetrahedron Lett., 28 (1987) 1333; J.M. Coxon and D.Q. McDonald, Tetrahedron Lett., 29 (1988) 2575; V.C. Ukachukwu and D.L. Whalen, Tetrahedron Lett., 29 (1988) 293; V.C. Ukachukwu, J.J. Blumenstein and D.L. Whalen, J. Am. Chem. Soc., 108 (1986) 5039; Y. Pocker, B.P. Ronald and K.W. Anderson, J. Am. Chem. Soc., 110 (1988) 6492; K. Maruoka, T. Ooi and H. Yamamoto, Tetrahedron, 48 (1992) 3303.
41. [18] B.N. Blackett, J.M. Coxon, M.P. Hartshorn and K.E. Richards, Tetrahedron, 25 (1969) 4999; B.N. Blackett, J.M. Coxon, M.P. Hartshorn and K.E. Richards, Australian J. Chem., 23 (1970) 2077; B.N. Blackett, J.M. Coxon, M.P. Hartshorn and K.E. Richards, J. Am. Chem. Soc., 92 (1970) 2574; J.M. Coxon and C.-E. Lim, Australian J. Chem., 30 (1977) 1137; J.W. Blunt, J.M. Coxon, C.-E. Lim and H.A. Schuyt, Australian J. Chem., 36 (1983) 97; J.M. Coxon and M.P. Hartshorn, Tetrahedron Lett., 28 (1987) 1333; J.M. Coxon and D.Q. McDonald, Tetrahedron Lett., 29 (1988) 2575; V.C. Ukachukwu and D.L. Whalen, Tetrahedron Lett., 29 (1988) 293; V.C. Ukachukwu, J.J. Blumenstein and D.L. Whalen, J. Am. Chem. Soc., 108 (1986) 5039; Y. Pocker, B.P. Ronald and K.W. Anderson, J. Am. Chem. Soc., 110 (1988) 6492; K. Maruoka, T. Ooi and H. Yamamoto, Tetrahedron, 48 (1992) 3303.
42. [18] B.N. Blackett, J.M. Coxon, M.P. Hartshorn and K.E. Richards, Tetrahedron, 25 (1969) 4999; B.N. Blackett, J.M. Coxon, M.P. Hartshorn and K.E. Richards, Australian J. Chem., 23 (1970) 2077; B.N. Blackett, J.M. Coxon, M.P. Hartshorn and K.E. Richards, J. Am. Chem. Soc., 92 (1970) 2574; J.M. Coxon and C.-E. Lim, Australian J. Chem., 30 (1977) 1137; J.W. Blunt, J.M. Coxon, C.-E. Lim and H.A. Schuyt, Australian J. Chem., 36 (1983) 97; J.M. Coxon and M.P. Hartshorn, Tetrahedron Lett., 28 (1987) 1333; J.M. Coxon and D.Q. McDonald, Tetrahedron Lett., 29 (1988) 2575; V.C. Ukachukwu and D.L. Whalen, Tetrahedron Lett., 29 (1988) 293; V.C. Ukachukwu, J.J. Blumenstein and D.L. Whalen, J. Am. Chem. Soc., 108 (1986) 5039; Y. Pocker, B.P. Ronald and K.W. Anderson, J. Am. Chem. Soc., 110 (1988) 6492; K. Maruoka, T. Ooi and H. Yamamoto, Tetrahedron, 48 (1992) 3303.
43. [18] B.N. Blackett, J.M. Coxon, M.P. Hartshorn and K.E. Richards, Tetrahedron, 25 (1969) 4999; B.N. Blackett, J.M. Coxon, M.P. Hartshorn and K.E. Richards, Australian J. Chem., 23 (1970) 2077; B.N. Blackett, J.M. Coxon, M.P. Hartshorn and K.E. Richards, J. Am. Chem. Soc., 92 (1970) 2574; J.M. Coxon and C.-E. Lim, Australian J. Chem., 30 (1977) 1137; J.W. Blunt, J.M. Coxon, C.-E. Lim and H.A. Schuyt, Australian J. Chem., 36 (1983) 97; J.M. Coxon and M.P. Hartshorn, Tetrahedron Lett., 28 (1987) 1333; J.M. Coxon and D.Q. McDonald, Tetrahedron Lett., 29 (1988) 2575; V.C. Ukachukwu and D.L. Whalen, Tetrahedron Lett., 29 (1988) 293; V.C. Ukachukwu, J.J. Blumenstein and D.L. Whalen, J. Am. Chem. Soc., 108 (1986) 5039; Y. Pocker, B.P. Ronald and K.W. Anderson, J. Am. Chem. Soc., 110 (1988) 6492; K. Maruoka, T. Ooi and H. Yamamoto, Tetrahedron, 48 (1992) 3303.
44. [18] B.N. Blackett, J.M. Coxon, M.P. Hartshorn and K.E. Richards, Tetrahedron, 25 (1969) 4999; B.N. Blackett, J.M. Coxon, M.P. Hartshorn and K.E. Richards, Australian J. Chem., 23 (1970) 2077; B.N. Blackett, J.M. Coxon, M.P. Hartshorn and K.E. Richards, J. Am. Chem. Soc., 92 (1970) 2574; J.M. Coxon and C.-E. Lim, Australian J. Chem., 30 (1977) 1137; J.W. Blunt, J.M. Coxon, C.-E. Lim and H.A. Schuyt, Australian J. Chem., 36 (1983) 97; J.M. Coxon and M.P. Hartshorn, Tetrahedron Lett., 28 (1987) 1333; J.M. Coxon and D.Q. McDonald, Tetrahedron Lett., 29 (1988) 2575; V.C. Ukachukwu and D.L. Whalen, Tetrahedron Lett., 29 (1988) 293; V.C. Ukachukwu, J.J. Blumenstein and D.L. Whalen, J. Am. Chem. Soc., 108 (1986) 5039; Y. Pocker, B.P. Ronald and K.W. Anderson, J. Am. Chem. Soc., 110 (1988) 6492; K. Maruoka, T. Ooi and H. Yamamoto, Tetrahedron, 48 (1992) 3303.
45. [18] B.N. Blackett, J.M. Coxon, M.P. Hartshorn and K.E. Richards, Tetrahedron, 25 (1969) 4999; B.N. Blackett, J.M. Coxon, M.P. Hartshorn and K.E. Richards, Australian J. Chem., 23 (1970) 2077; B.N. Blackett, J.M. Coxon, M.P. Hartshorn and K.E. Richards, J. Am. Chem. Soc., 92 (1970) 2574; J.M. Coxon and C.-E. Lim, Australian J. Chem., 30 (1977) 1137; J.W. Blunt, J.M. Coxon, C.-E. Lim and H.A. Schuyt, Australian J. Chem., 36 (1983) 97; J.M. Coxon and M.P. Hartshorn, Tetrahedron Lett., 28 (1987) 1333; J.M. Coxon and D.Q. McDonald, Tetrahedron Lett., 29 (1988) 2575; V.C. Ukachukwu and D.L. Whalen, Tetrahedron Lett., 29 (1988) 293; V.C. Ukachukwu, J.J. Blumenstein and D.L. Whalen, J. Am. Chem. Soc., 108 (1986) 5039; Y. Pocker, B.P. Ronald and K.W. Anderson, J. Am. Chem. Soc., 110 (1988) 6492; K. Maruoka, T. Ooi and H. Yamamoto, Tetrahedron, 48 (1992) 3303.
46. [18] B.N. Blackett, J.M. Coxon, M.P. Hartshorn and K.E. Richards, Tetrahedron, 25 (1969) 4999; B.N. Blackett, J.M. Coxon, M.P. Hartshorn and K.E. Richards, Australian J. Chem., 23 (1970) 2077; B.N. Blackett, J.M. Coxon, M.P. Hartshorn and K.E. Richards, J. Am. Chem. Soc., 92 (1970) 2574; J.M. Coxon and C.-E. Lim, Australian J. Chem., 30 (1977) 1137; J.W. Blunt, J.M. Coxon, C.-E. Lim and H.A. Schuyt, Australian J. Chem., 36 (1983) 97; J.M. Coxon and M.P. Hartshorn, Tetrahedron Lett., 28 (1987) 1333; J.M. Coxon and D.Q. McDonald, Tetrahedron Lett., 29 (1988) 2575; V.C. Ukachukwu and D.L. Whalen, Tetrahedron Lett., 29 (1988) 293; V.C. Ukachukwu, J.J. Blumenstein and D.L. Whalen, J. Am. Chem. Soc., 108 (1986) 5039; Y. Pocker, B.P. Ronald and K.W. Anderson, J. Am. Chem. Soc., 110 (1988) 6492; K. Maruoka, T. Ooi and H. Yamamoto, Tetrahedron, 48 (1992) 3303.
47. [19] R.E. Shepherd, Inorg. Chim. Acta, 209 (1993) 201; L.M. Atagi, D.E. Over, D.R. McAlister and J.M. Mayer, J. Am. Chem. Soc., 113 (1991) 870; J.K. Kochi, D.M. Singleton and L.J. Andrews, Tetrahedron, 24 (1968) 3503; J.E. McMurry and M.P. Fleming, J. Org. Chem., 40 (1975) 2555.
48. [19] R.E. Shepherd, Inorg. Chim. Acta, 209 (1993) 201; L.M. Atagi, D.E. Over, D.R. McAlister and J.M. Mayer, J. Am. Chem. Soc., 113 (1991) 870; J.K. Kochi, D.M. Singleton and L.J. Andrews, Tetrahedron, 24 (1968) 3503; J.E. McMurry and M.P. Fleming, J. Org. Chem., 40 (1975) 2555.
49. [19] R.E. Shepherd, Inorg. Chim. Acta, 209 (1993) 201; L.M. Atagi, D.E. Over, D.R. McAlister and J.M. Mayer, J. Am. Chem. Soc., 113 (1991) 870; J.K. Kochi, D.M. Singleton and L.J. Andrews, Tetrahedron, 24 (1968) 3503; J.E. McMurry and M.P. Fleming, J. Org. Chem., 40 (1975) 2555.
50. [19] R.E. Shepherd, Inorg. Chim. Acta, 209 (1993) 201; L.M. Atagi, D.E. Over, D.R. McAlister and J.M. Mayer, J. Am. Chem. Soc., 113 (1991) 870; J.K. Kochi, D.M. Singleton and L.J. Andrews, Tetrahedron, 24 (1968) 3503; J.E. McMurry and M.P. Fleming, J. Org. Chem., 40 (1975) 2555.
51. [20] J.T. Groves, K.-H. Ahn and R. Quinn, J. Am. Chem. Soc., 110 (1988) 4217; T.V. RajaBabu and W.A. Nugent, J. Am. Chem. Soc., 116 (1994) 986.
52. [20] J.T. Groves, K.-H. Ahn and R. Quinn, J. Am. Chem. Soc., 110 (1988) 4217; T.V. RajaBabu and W.A. Nugent, J. Am. Chem. Soc., 116 (1994) 986.
53. [21] H. Sakurai, A. Okada, M. Kira and K. Yonezawa, Tetrahedron Lett., (1971) 1511; H. Sakurai, A. Okada, H. Umino and M. Kira, J. Am. Chem. Soc., 95 (1973) 955; H. Sakurai and F. Kondo, J. Organomet. Chem., 92 (1975) C46; A.G. Brook, R.K.M. Kallury and Y.C. Poon, Organometallics, 1 (1982) 987.
54. [21] H. Sakurai, A. Okada, M. Kira and K. Yonezawa, Tetrahedron Lett., (1971) 1511; H. Sakurai, A. Okada, H. Umino and M. Kira, J. Am. Chem. Soc., 95 (1973) 955; H. Sakurai and F. Kondo, J. Organomet. Chem., 92 (1975) C46; A.G. Brook, R.K.M. Kallury and Y.C. Poon, Organometallics, 1 (1982) 987.
55. [21] H. Sakurai, A. Okada, M. Kira and K. Yonezawa, Tetrahedron Lett., (1971) 1511; H. Sakurai, A. Okada, H. Umino and M. Kira, J. Am. Chem. Soc., 95 (1973) 955; H. Sakurai and F. Kondo, J. Organomet. Chem., 92 (1975) C46; A.G. Brook, R.K.M. Kallury and Y.C. Poon, Organometallics, 1 (1982) 987.
56. [21] H. Sakurai, A. Okada, M. Kira and K. Yonezawa, Tetrahedron Lett., (1971) 1511; H. Sakurai, A. Okada, H. Umino and M. Kira, J. Am. Chem. Soc., 95 (1973) 955; H. Sakurai and F. Kondo, J. Organomet. Chem., 92 (1975) C46; A.G. Brook, R.K.M. Kallury and Y.C. Poon, Organometallics, 1 (1982) 987.
57. [22] K. Boujlel and J. Simonet, Electrochim. Acta, 24 (1979) 481; K. Boujlel, P. Martigny and J. Simonet, J. Electroanal. Chem., 144 (1983) 437.
58. [22] K. Boujlel and J. Simonet, Electrochim. Acta, 24 (1979) 481; K. Boujlel, P. Martigny and J. Simonet, J. Electroanal. Chem., 144 (1983) 437.
59. [23] W. Kaim, Acc. Chem. Res., 18 (1985) 160.
60. [24] R.P. Tan, G.R. Gillette, H.B. Yokelson and R. West, Inorg. Synth., 29 (1992) 19.
61. [25] D.J. Pasto and C.C. Cumbo, J. Org. Chem., 30 (1965) 1271.
62. [26] E.J. Corey and M. Chaykovsky, J. Am. Chem. Soc., 87 (1965) 1353.
63. 2H, see Ref. [2].
64. [28] G.M. Sheldrick, Acta Crystallogr., A46 (1990) 467.
65. [29] G.M. Sheldrick, J. Appl. Crystallogr., (1995), in press.
66. [30] A.C. Larsen, in F.K. Ahmed (ed.), Crystallographic Computing, Mundsgaard, Copenhagen, 1970, pp. 291-294.
67. [31] For 6a: International Tables for X-ray Crystallography, Kynoch Press, Birmingham, UK, 1974, Vol. IV, Table 2.3.1 and 1992, Vol. C, Table 6.1.1.4 (present distributor Kluwer Academic). For 6g: International Tables for X-ray Crystallography, Kluwer, Boston, 1992, Vol. C, Tables 6.1.1.4 and 4.2.6.8.
68. [31] For 6a: International Tables for X-ray Crystallography, Kynoch Press, Birmingham, UK, 1974, Vol. IV, Table 2.3.1 and 1992, Vol. C, Table 6.1.1.4 (present distributor Kluwer Academic). For 6g: International Tables for X-ray Crystallography, Kluwer, Boston, 1992, Vol. C, Tables 6.1.1.4 and 4.2.6.8.