Unimolecular rearrangement of α-silylcarbenium ions. An ab initio study

Journal of Organometallic Chemistry

Volumn 510, Issue 1-2, 1996, Pages 25-35

  Cho, Soo Gyeong ^a  

^a Agency for Defence Development   (South Korea)

Author keywords

Ab initio; Gaussian calculations; Molecular mechanics; Rearrangement; Silicon

Indexed keywords

EID: 0030596365     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0022-328X(95)05887-U     Document Type: Article

References (73)

1. For reviews, see: (a) J. Pola, in V. Chavalovsky and J.B. Bellama (eds.), Carbon-Functional Organosilicon Compounds, Plenum, New York, 1984, Chap 2; (b) A.G. Brook and A.R. Bassindale, in Rearrangements in Ground and Excited States, Academic Press Inc., New York, 1980, p. 149.
2. For reviews, see: (a) J. Pola, in V. Chavalovsky and J.B. Bellama (eds.), Carbon-Functional Organosilicon Compounds, Plenum, New York, 1984, Chap 2; (b) A.G. Brook and A.R. Bassindale, in Rearrangements in Ground and Excited States, Academic Press Inc., New York, 1980, p. 149.
3. For the thermal rearrangement, see: (a) A.G. Brook and P.F. Jones, Chem. Commun., (1969) 1324; (b) D. Seyferth and F.M. Armbrecht, Jr., J. Am. Chem. Soc., 91 (1969) 2616; (c) A.R. Bassindale, A.G. Brook, P.F. Jones and J.M. Lennon, Can. J. Chem., 53 (1975) 332; (d) J.G. Martin, M.A. Ring and H.E. O'Neal, Organometallics, 5 (1986) 1228; (e) I.M.T. Davidson and S. Ijadi-Maghsoodi, Organometallics, 5 (1986) 2086; (f) G.L. Larson, R. Klesse and F.K. Cartledge, Organometallics, 6 (1987) 2250; (g) R. Klesse, Ph.D. Dissertation, University of Puerto Rico, 1987; (h) M.P. Clarke, R. Damrauer, I.M.T. Davidson and R. Simon, Organometallics, 8 (1989) 2031.
4. For the thermal rearrangement, see: (a) A.G. Brook and P.F. Jones, Chem. Commun., (1969) 1324; (b) D. Seyferth and F.M. Armbrecht, Jr., J. Am. Chem. Soc., 91 (1969) 2616; (c) A.R. Bassindale, A.G. Brook, P.F. Jones and J.M. Lennon, Can. J. Chem., 53 (1975) 332; (d) J.G. Martin, M.A. Ring and H.E. O'Neal, Organometallics, 5 (1986) 1228; (e) I.M.T. Davidson and S. Ijadi-Maghsoodi, Organometallics, 5 (1986) 2086; (f) G.L. Larson, R. Klesse and F.K. Cartledge, Organometallics, 6 (1987) 2250; (g) R. Klesse, Ph.D. Dissertation, University of Puerto Rico, 1987; (h) M.P. Clarke, R. Damrauer, I.M.T. Davidson and R. Simon, Organometallics, 8 (1989) 2031.
5. For the thermal rearrangement, see: (a) A.G. Brook and P.F. Jones, Chem. Commun., (1969) 1324; (b) D. Seyferth and F.M. Armbrecht, Jr., J. Am. Chem. Soc., 91 (1969) 2616; (c) A.R. Bassindale, A.G. Brook, P.F. Jones and J.M. Lennon, Can. J. Chem., 53 (1975) 332; (d) J.G. Martin, M.A. Ring and H.E. O'Neal, Organometallics, 5 (1986) 1228; (e) I.M.T. Davidson and S. Ijadi-Maghsoodi, Organometallics, 5 (1986) 2086; (f) G.L. Larson, R. Klesse and F.K. Cartledge, Organometallics, 6 (1987) 2250; (g) R. Klesse, Ph.D. Dissertation, University of Puerto Rico, 1987; (h) M.P. Clarke, R. Damrauer, I.M.T. Davidson and R. Simon, Organometallics, 8 (1989) 2031.
6. For the thermal rearrangement, see: (a) A.G. Brook and P.F. Jones, Chem. Commun., (1969) 1324; (b) D. Seyferth and F.M. Armbrecht, Jr., J. Am. Chem. Soc., 91 (1969) 2616; (c) A.R. Bassindale, A.G. Brook, P.F. Jones and J.M. Lennon, Can. J. Chem., 53 (1975) 332; (d) J.G. Martin, M.A. Ring and H.E. O'Neal, Organometallics, 5 (1986) 1228; (e) I.M.T. Davidson and S. Ijadi-Maghsoodi, Organometallics, 5 (1986) 2086; (f) G.L. Larson, R. Klesse and F.K. Cartledge, Organometallics, 6 (1987) 2250; (g) R. Klesse, Ph.D. Dissertation, University of Puerto Rico, 1987; (h) M.P. Clarke, R. Damrauer, I.M.T. Davidson and R. Simon, Organometallics, 8 (1989) 2031.
7. For the thermal rearrangement, see: (a) A.G. Brook and P.F. Jones, Chem. Commun., (1969) 1324; (b) D. Seyferth and F.M. Armbrecht, Jr., J. Am. Chem. Soc., 91 (1969) 2616; (c) A.R. Bassindale, A.G. Brook, P.F. Jones and J.M. Lennon, Can. J. Chem., 53 (1975) 332; (d) J.G. Martin, M.A. Ring and H.E. O'Neal, Organometallics, 5 (1986) 1228; (e) I.M.T. Davidson and S. Ijadi-Maghsoodi, Organometallics, 5 (1986) 2086; (f) G.L. Larson, R. Klesse and F.K. Cartledge, Organometallics, 6 (1987) 2250; (g) R. Klesse, Ph.D. Dissertation, University of Puerto Rico, 1987; (h) M.P. Clarke, R. Damrauer, I.M.T. Davidson and R. Simon, Organometallics, 8 (1989) 2031.
8. For the thermal rearrangement, see: (a) A.G. Brook and P.F. Jones, Chem. Commun., (1969) 1324; (b) D. Seyferth and F.M. Armbrecht, Jr., J. Am. Chem. Soc., 91 (1969) 2616; (c) A.R. Bassindale, A.G. Brook, P.F. Jones and J.M. Lennon, Can. J. Chem., 53 (1975) 332; (d) J.G. Martin, M.A. Ring and H.E. O'Neal, Organometallics, 5 (1986) 1228; (e) I.M.T. Davidson and S. Ijadi-Maghsoodi, Organometallics, 5 (1986) 2086; (f) G.L. Larson, R. Klesse and F.K. Cartledge, Organometallics, 6 (1987) 2250; (g) R. Klesse, Ph.D. Dissertation, University of Puerto Rico, 1987; (h) M.P. Clarke, R. Damrauer, I.M.T. Davidson and R. Simon, Organometallics, 8 (1989) 2031.
9. For the thermal rearrangement, see: (a) A.G. Brook and P.F. Jones, Chem. Commun., (1969) 1324; (b) D. Seyferth and F.M. Armbrecht, Jr., J. Am. Chem. Soc., 91 (1969) 2616; (c) A.R. Bassindale, A.G. Brook, P.F. Jones and J.M. Lennon, Can. J. Chem., 53 (1975) 332; (d) J.G. Martin, M.A. Ring and H.E. O'Neal, Organometallics, 5 (1986) 1228; (e) I.M.T. Davidson and S. Ijadi-Maghsoodi, Organometallics, 5 (1986) 2086; (f) G.L. Larson, R. Klesse and F.K. Cartledge, Organometallics, 6 (1987) 2250; (g) R. Klesse, Ph.D. Dissertation, University of Puerto Rico, 1987; (h) M.P. Clarke, R. Damrauer, I.M.T. Davidson and R. Simon, Organometallics, 8 (1989) 2031.
10. For the thermal rearrangement, see: (a) A.G. Brook and P.F. Jones, Chem. Commun., (1969) 1324; (b) D. Seyferth and F.M. Armbrecht, Jr., J. Am. Chem. Soc., 91 (1969) 2616; (c) A.R. Bassindale, A.G. Brook, P.F. Jones and J.M. Lennon, Can. J. Chem., 53 (1975) 332; (d) J.G. Martin, M.A. Ring and H.E. O'Neal, Organometallics, 5 (1986) 1228; (e) I.M.T. Davidson and S. Ijadi-Maghsoodi, Organometallics, 5 (1986) 2086; (f) G.L. Larson, R. Klesse and F.K. Cartledge, Organometallics, 6 (1987) 2250; (g) R. Klesse, Ph.D. Dissertation, University of Puerto Rico, 1987; (h) M.P. Clarke, R. Damrauer, I.M.T. Davidson and R. Simon, Organometallics, 8 (1989) 2031.
11. For the Lewis acid-catalyzed rearrangement, see: (a) F.C. Whitmore, L.H. Sommer and J. Gold, J. Am. Chem. Soc., 69 (1949) 1976; (b) L.H. Sommer, D.L. Bailey, J.R. Gould and F.C. Whitemore, J. Am. Chem. Soc., 76 (1954) 801; (c) M. Kumada, J.-I. Nakajima, M. Ishikawa and Y. Yamamoto, J. Org. Chem., 23 (1958) 292; (d) M. Kumada and M. Ishikawa, J. Organomet. Chem., 1 (1964) 411; (e) M. Kumada, M. Ishikawa, S. Maeda and K. Ikura. J. Organomet. Chem., 2 (1964) 146; (f) A.G. Brook, K.H. Pannell, G.E. LeGrow and J.J. Sheeto, J. Organomet. Chem., 2 (1964) 491; (g) R.W. Bott, C. Eaborn and B.M. Rushton, J. Organomet. Chem., 3 (1965) 455; (h) O.W. Steward, W.J. Unl and B.W. Sands, J. Organomet. Chem., 15 (1968) 329; (i) W.I. Beven, R.N. Haszeldine, J. Middleton and A.E. Tipping, J. Organomet. Chem., 23 (1970) C17; (j) T.J. Hairston and D.H. O'Brien, J. Organomet. Chem., 29 (1971) 79; (k) K. Tamao, T. Nakajima and M. Kumata, Organometallics, 3 (1984) 1655; (l) L.R. Robinson, G.T. Burns and T.J. Barton, J. Am. Chem. Soc., 107 (1985) 3935; (m) G. Märkl, M. Horn and W. Schlosser, Tetrahedron Lett., 27 (1986) 4019; (n) L. Shui, M.S. Thesis, Louisiana State University, 1987; (o) S.G. Cho, F.K. Cartledge. R.J. Unwalla and S. Profeta, Jr., Tetrahedron, 46 (1990) 8005; (p) S.G. Cho, Bull. Korean Chem. Soc., 13 (1994) 183.
12. For the Lewis acid-catalyzed rearrangement, see: (a) F.C. Whitmore, L.H. Sommer and J. Gold, J. Am. Chem. Soc., 69 (1949) 1976; (b) L.H. Sommer, D.L. Bailey, J.R. Gould and F.C. Whitemore, J. Am. Chem. Soc., 76 (1954) 801; (c) M. Kumada, J.-I. Nakajima, M. Ishikawa and Y. Yamamoto, J. Org. Chem., 23 (1958) 292; (d) M. Kumada and M. Ishikawa, J. Organomet. Chem., 1 (1964) 411; (e) M. Kumada, M. Ishikawa, S. Maeda and K. Ikura. J. Organomet. Chem., 2 (1964) 146; (f) A.G. Brook, K.H. Pannell, G.E. LeGrow and J.J. Sheeto, J. Organomet. Chem., 2 (1964) 491; (g) R.W. Bott, C. Eaborn and B.M. Rushton, J. Organomet. Chem., 3 (1965) 455; (h) O.W. Steward, W.J. Unl and B.W. Sands, J. Organomet. Chem., 15 (1968) 329; (i) W.I. Beven, R.N. Haszeldine, J. Middleton and A.E. Tipping, J. Organomet. Chem., 23 (1970) C17; (j) T.J. Hairston and D.H. O'Brien, J. Organomet. Chem., 29 (1971) 79; (k) K. Tamao, T. Nakajima and M. Kumata, Organometallics, 3 (1984) 1655; (l) L.R. Robinson, G.T. Burns and T.J. Barton, J. Am. Chem. Soc., 107 (1985) 3935; (m) G. Märkl, M. Horn and W. Schlosser, Tetrahedron Lett., 27 (1986) 4019; (n) L. Shui, M.S. Thesis, Louisiana State University, 1987; (o) S.G. Cho, F.K. Cartledge. R.J. Unwalla and S. Profeta, Jr., Tetrahedron, 46 (1990) 8005; (p) S.G. Cho, Bull. Korean Chem. Soc., 13 (1994) 183.
13. For the Lewis acid-catalyzed rearrangement, see: (a) F.C. Whitmore, L.H. Sommer and J. Gold, J. Am. Chem. Soc., 69 (1949) 1976; (b) L.H. Sommer, D.L. Bailey, J.R. Gould and F.C. Whitemore, J. Am. Chem. Soc., 76 (1954) 801; (c) M. Kumada, J.-I. Nakajima, M. Ishikawa and Y. Yamamoto, J. Org. Chem., 23 (1958) 292; (d) M. Kumada and M. Ishikawa, J. Organomet. Chem., 1 (1964) 411; (e) M. Kumada, M. Ishikawa, S. Maeda and K. Ikura. J. Organomet. Chem., 2 (1964) 146; (f) A.G. Brook, K.H. Pannell, G.E. LeGrow and J.J. Sheeto, J. Organomet. Chem., 2 (1964) 491; (g) R.W. Bott, C. Eaborn and B.M. Rushton, J. Organomet. Chem., 3 (1965) 455; (h) O.W. Steward, W.J. Unl and B.W. Sands, J. Organomet. Chem., 15 (1968) 329; (i) W.I. Beven, R.N. Haszeldine, J. Middleton and A.E. Tipping, J. Organomet. Chem., 23 (1970) C17; (j) T.J. Hairston and D.H. O'Brien, J. Organomet. Chem., 29 (1971) 79; (k) K. Tamao, T. Nakajima and M. Kumata, Organometallics, 3 (1984) 1655; (l) L.R. Robinson, G.T. Burns and T.J. Barton, J. Am. Chem. Soc., 107 (1985) 3935; (m) G. Märkl, M. Horn and W. Schlosser, Tetrahedron Lett., 27 (1986) 4019; (n) L. Shui, M.S. Thesis, Louisiana State University, 1987; (o) S.G. Cho, F.K. Cartledge. R.J. Unwalla and S. Profeta, Jr., Tetrahedron, 46 (1990) 8005; (p) S.G. Cho, Bull. Korean Chem. Soc., 13 (1994) 183.
14. For the Lewis acid-catalyzed rearrangement, see: (a) F.C. Whitmore, L.H. Sommer and J. Gold, J. Am. Chem. Soc., 69 (1949) 1976; (b) L.H. Sommer, D.L. Bailey, J.R. Gould and F.C. Whitemore, J. Am. Chem. Soc., 76 (1954) 801; (c) M. Kumada, J.-I. Nakajima, M. Ishikawa and Y. Yamamoto, J. Org. Chem., 23 (1958) 292; (d) M. Kumada and M. Ishikawa, J. Organomet. Chem., 1 (1964) 411; (e) M. Kumada, M. Ishikawa, S. Maeda and K. Ikura. J. Organomet. Chem., 2 (1964) 146; (f) A.G. Brook, K.H. Pannell, G.E. LeGrow and J.J. Sheeto, J. Organomet. Chem., 2 (1964) 491; (g) R.W. Bott, C. Eaborn and B.M. Rushton, J. Organomet. Chem., 3 (1965) 455; (h) O.W. Steward, W.J. Unl and B.W. Sands, J. Organomet. Chem., 15 (1968) 329; (i) W.I. Beven, R.N. Haszeldine, J. Middleton and A.E. Tipping, J. Organomet. Chem., 23 (1970) C17; (j) T.J. Hairston and D.H. O'Brien, J. Organomet. Chem., 29 (1971) 79; (k) K. Tamao, T. Nakajima and M. Kumata, Organometallics, 3 (1984) 1655; (l) L.R. Robinson, G.T. Burns and T.J. Barton, J. Am. Chem. Soc., 107 (1985) 3935; (m) G. Märkl, M. Horn and W. Schlosser, Tetrahedron Lett., 27 (1986) 4019; (n) L. Shui, M.S. Thesis, Louisiana State University, 1987; (o) S.G. Cho, F.K. Cartledge. R.J. Unwalla and S. Profeta, Jr., Tetrahedron, 46 (1990) 8005; (p) S.G. Cho, Bull. Korean Chem. Soc., 13 (1994) 183.
15. For the Lewis acid-catalyzed rearrangement, see: (a) F.C. Whitmore, L.H. Sommer and J. Gold, J. Am. Chem. Soc., 69 (1949) 1976; (b) L.H. Sommer, D.L. Bailey, J.R. Gould and F.C. Whitemore, J. Am. Chem. Soc., 76 (1954) 801; (c) M. Kumada, J.-I. Nakajima, M. Ishikawa and Y. Yamamoto, J. Org. Chem., 23 (1958) 292; (d) M. Kumada and M. Ishikawa, J. Organomet. Chem., 1 (1964) 411; (e) M. Kumada, M. Ishikawa, S. Maeda and K. Ikura. J. Organomet. Chem., 2 (1964) 146; (f) A.G. Brook, K.H. Pannell, G.E. LeGrow and J.J. Sheeto, J. Organomet. Chem., 2 (1964) 491; (g) R.W. Bott, C. Eaborn and B.M. Rushton, J. Organomet. Chem., 3 (1965) 455; (h) O.W. Steward, W.J. Unl and B.W. Sands, J. Organomet. Chem., 15 (1968) 329; (i) W.I. Beven, R.N. Haszeldine, J. Middleton and A.E. Tipping, J. Organomet. Chem., 23 (1970) C17; (j) T.J. Hairston and D.H. O'Brien, J. Organomet. Chem., 29 (1971) 79; (k) K. Tamao, T. Nakajima and M. Kumata, Organometallics, 3 (1984) 1655; (l) L.R. Robinson, G.T. Burns and T.J. Barton, J. Am. Chem. Soc., 107 (1985) 3935; (m) G. Märkl, M. Horn and W. Schlosser, Tetrahedron Lett., 27 (1986) 4019; (n) L. Shui, M.S. Thesis, Louisiana State University, 1987; (o) S.G. Cho, F.K. Cartledge. R.J. Unwalla and S. Profeta, Jr., Tetrahedron, 46 (1990) 8005; (p) S.G. Cho, Bull. Korean Chem. Soc., 13 (1994) 183.
16. For the Lewis acid-catalyzed rearrangement, see: (a) F.C. Whitmore, L.H. Sommer and J. Gold, J. Am. Chem. Soc., 69 (1949) 1976; (b) L.H. Sommer, D.L. Bailey, J.R. Gould and F.C. Whitemore, J. Am. Chem. Soc., 76 (1954) 801; (c) M. Kumada, J.-I. Nakajima, M. Ishikawa and Y. Yamamoto, J. Org. Chem., 23 (1958) 292; (d) M. Kumada and M. Ishikawa, J. Organomet. Chem., 1 (1964) 411; (e) M. Kumada, M. Ishikawa, S. Maeda and K. Ikura. J. Organomet. Chem., 2 (1964) 146; (f) A.G. Brook, K.H. Pannell, G.E. LeGrow and J.J. Sheeto, J. Organomet. Chem., 2 (1964) 491; (g) R.W. Bott, C. Eaborn and B.M. Rushton, J. Organomet. Chem., 3 (1965) 455; (h) O.W. Steward, W.J. Unl and B.W. Sands, J. Organomet. Chem., 15 (1968) 329; (i) W.I. Beven, R.N. Haszeldine, J. Middleton and A.E. Tipping, J. Organomet. Chem., 23 (1970) C17; (j) T.J. Hairston and D.H. O'Brien, J. Organomet. Chem., 29 (1971) 79; (k) K. Tamao, T. Nakajima and M. Kumata, Organometallics, 3 (1984) 1655; (l) L.R. Robinson, G.T. Burns and T.J. Barton, J. Am. Chem. Soc., 107 (1985) 3935; (m) G. Märkl, M. Horn and W. Schlosser, Tetrahedron Lett., 27 (1986) 4019; (n) L. Shui, M.S. Thesis, Louisiana State University, 1987; (o) S.G. Cho, F.K. Cartledge. R.J. Unwalla and S. Profeta, Jr., Tetrahedron, 46 (1990) 8005; (p) S.G. Cho, Bull. Korean Chem. Soc., 13 (1994) 183.
17. For the Lewis acid-catalyzed rearrangement, see: (a) F.C. Whitmore, L.H. Sommer and J. Gold, J. Am. Chem. Soc., 69 (1949) 1976; (b) L.H. Sommer, D.L. Bailey, J.R. Gould and F.C. Whitemore, J. Am. Chem. Soc., 76 (1954) 801; (c) M. Kumada, J.-I. Nakajima, M. Ishikawa and Y. Yamamoto, J. Org. Chem., 23 (1958) 292; (d) M. Kumada and M. Ishikawa, J. Organomet. Chem., 1 (1964) 411; (e) M. Kumada, M. Ishikawa, S. Maeda and K. Ikura. J. Organomet. Chem., 2 (1964) 146; (f) A.G. Brook, K.H. Pannell, G.E. LeGrow and J.J. Sheeto, J. Organomet. Chem., 2 (1964) 491; (g) R.W. Bott, C. Eaborn and B.M. Rushton, J. Organomet. Chem., 3 (1965) 455; (h) O.W. Steward, W.J. Unl and B.W. Sands, J. Organomet. Chem., 15 (1968) 329; (i) W.I. Beven, R.N. Haszeldine, J. Middleton and A.E. Tipping, J. Organomet. Chem., 23 (1970) C17; (j) T.J. Hairston and D.H. O'Brien, J. Organomet. Chem., 29 (1971) 79; (k) K. Tamao, T. Nakajima and M. Kumata, Organometallics, 3 (1984) 1655; (l) L.R. Robinson, G.T. Burns and T.J. Barton, J. Am. Chem. Soc., 107 (1985) 3935; (m) G. Märkl, M. Horn and W. Schlosser, Tetrahedron Lett., 27 (1986) 4019; (n) L. Shui, M.S. Thesis, Louisiana State University, 1987; (o) S.G. Cho, F.K. Cartledge. R.J. Unwalla and S. Profeta, Jr., Tetrahedron, 46 (1990) 8005; (p) S.G. Cho, Bull. Korean Chem. Soc., 13 (1994) 183.
18. For the Lewis acid-catalyzed rearrangement, see: (a) F.C. Whitmore, L.H. Sommer and J. Gold, J. Am. Chem. Soc., 69 (1949) 1976; (b) L.H. Sommer, D.L. Bailey, J.R. Gould and F.C. Whitemore, J. Am. Chem. Soc., 76 (1954) 801; (c) M. Kumada, J.-I. Nakajima, M. Ishikawa and Y. Yamamoto, J. Org. Chem., 23 (1958) 292; (d) M. Kumada and M. Ishikawa, J. Organomet. Chem., 1 (1964) 411; (e) M. Kumada, M. Ishikawa, S. Maeda and K. Ikura. J. Organomet. Chem., 2 (1964) 146; (f) A.G. Brook, K.H. Pannell, G.E. LeGrow and J.J. Sheeto, J. Organomet. Chem., 2 (1964) 491; (g) R.W. Bott, C. Eaborn and B.M. Rushton, J. Organomet. Chem., 3 (1965) 455; (h) O.W. Steward, W.J. Unl and B.W. Sands, J. Organomet. Chem., 15 (1968) 329; (i) W.I. Beven, R.N. Haszeldine, J. Middleton and A.E. Tipping, J. Organomet. Chem., 23 (1970) C17; (j) T.J. Hairston and D.H. O'Brien, J. Organomet. Chem., 29 (1971) 79; (k) K. Tamao, T. Nakajima and M. Kumata, Organometallics, 3 (1984) 1655; (l) L.R. Robinson, G.T. Burns and T.J. Barton, J. Am. Chem. Soc., 107 (1985) 3935; (m) G. Märkl, M. Horn and W. Schlosser, Tetrahedron Lett., 27 (1986) 4019; (n) L. Shui, M.S. Thesis, Louisiana State University, 1987; (o) S.G. Cho, F.K. Cartledge. R.J. Unwalla and S. Profeta, Jr., Tetrahedron, 46 (1990) 8005; (p) S.G. Cho, Bull. Korean Chem. Soc., 13 (1994) 183.
19. For the Lewis acid-catalyzed rearrangement, see: (a) F.C. Whitmore, L.H. Sommer and J. Gold, J. Am. Chem. Soc., 69 (1949) 1976; (b) L.H. Sommer, D.L. Bailey, J.R. Gould and F.C. Whitemore, J. Am. Chem. Soc., 76 (1954) 801; (c) M. Kumada, J.-I. Nakajima, M. Ishikawa and Y. Yamamoto, J. Org. Chem., 23 (1958) 292; (d) M. Kumada and M. Ishikawa, J. Organomet. Chem., 1 (1964) 411; (e) M. Kumada, M. Ishikawa, S. Maeda and K. Ikura. J. Organomet. Chem., 2 (1964) 146; (f) A.G. Brook, K.H. Pannell, G.E. LeGrow and J.J. Sheeto, J. Organomet. Chem., 2 (1964) 491; (g) R.W. Bott, C. Eaborn and B.M. Rushton, J. Organomet. Chem., 3 (1965) 455; (h) O.W. Steward, W.J. Unl and B.W. Sands, J. Organomet. Chem., 15 (1968) 329; (i) W.I. Beven, R.N. Haszeldine, J. Middleton and A.E. Tipping, J. Organomet. Chem., 23 (1970) C17; (j) T.J. Hairston and D.H. O'Brien, J. Organomet. Chem., 29 (1971) 79; (k) K. Tamao, T. Nakajima and M. Kumata, Organometallics, 3 (1984) 1655; (l) L.R. Robinson, G.T. Burns and T.J. Barton, J. Am. Chem. Soc., 107 (1985) 3935; (m) G. Märkl, M. Horn and W. Schlosser, Tetrahedron Lett., 27 (1986) 4019; (n) L. Shui, M.S. Thesis, Louisiana State University, 1987; (o) S.G. Cho, F.K. Cartledge. R.J. Unwalla and S. Profeta, Jr., Tetrahedron, 46 (1990) 8005; (p) S.G. Cho, Bull. Korean Chem. Soc., 13 (1994) 183.
20. For the Lewis acid-catalyzed rearrangement, see: (a) F.C. Whitmore, L.H. Sommer and J. Gold, J. Am. Chem. Soc., 69 (1949) 1976; (b) L.H. Sommer, D.L. Bailey, J.R. Gould and F.C. Whitemore, J. Am. Chem. Soc., 76 (1954) 801; (c) M. Kumada, J.-I. Nakajima, M. Ishikawa and Y. Yamamoto, J. Org. Chem., 23 (1958) 292; (d) M. Kumada and M. Ishikawa, J. Organomet. Chem., 1 (1964) 411; (e) M. Kumada, M. Ishikawa, S. Maeda and K. Ikura. J. Organomet. Chem., 2 (1964) 146; (f) A.G. Brook, K.H. Pannell, G.E. LeGrow and J.J. Sheeto, J. Organomet. Chem., 2 (1964) 491; (g) R.W. Bott, C. Eaborn and B.M. Rushton, J. Organomet. Chem., 3 (1965) 455; (h) O.W. Steward, W.J. Unl and B.W. Sands, J. Organomet. Chem., 15 (1968) 329; (i) W.I. Beven, R.N. Haszeldine, J. Middleton and A.E. Tipping, J. Organomet. Chem., 23 (1970) C17; (j) T.J. Hairston and D.H. O'Brien, J. Organomet. Chem., 29 (1971) 79; (k) K. Tamao, T. Nakajima and M. Kumata, Organometallics, 3 (1984) 1655; (l) L.R. Robinson, G.T. Burns and T.J. Barton, J. Am. Chem. Soc., 107 (1985) 3935; (m) G. Märkl, M. Horn and W. Schlosser, Tetrahedron Lett., 27 (1986) 4019; (n) L. Shui, M.S. Thesis, Louisiana State University, 1987; (o) S.G. Cho, F.K. Cartledge. R.J. Unwalla and S. Profeta, Jr., Tetrahedron, 46 (1990) 8005; (p) S.G. Cho, Bull. Korean Chem. Soc., 13 (1994) 183.
21. For the Lewis acid-catalyzed rearrangement, see: (a) F.C. Whitmore, L.H. Sommer and J. Gold, J. Am. Chem. Soc., 69 (1949) 1976; (b) L.H. Sommer, D.L. Bailey, J.R. Gould and F.C. Whitemore, J. Am. Chem. Soc., 76 (1954) 801; (c) M. Kumada, J.-I. Nakajima, M. Ishikawa and Y. Yamamoto, J. Org. Chem., 23 (1958) 292; (d) M. Kumada and M. Ishikawa, J. Organomet. Chem., 1 (1964) 411; (e) M. Kumada, M. Ishikawa, S. Maeda and K. Ikura. J. Organomet. Chem., 2 (1964) 146; (f) A.G. Brook, K.H. Pannell, G.E. LeGrow and J.J. Sheeto, J. Organomet. Chem., 2 (1964) 491; (g) R.W. Bott, C. Eaborn and B.M. Rushton, J. Organomet. Chem., 3 (1965) 455; (h) O.W. Steward, W.J. Unl and B.W. Sands, J. Organomet. Chem., 15 (1968) 329; (i) W.I. Beven, R.N. Haszeldine, J. Middleton and A.E. Tipping, J. Organomet. Chem., 23 (1970) C17; (j) T.J. Hairston and D.H. O'Brien, J. Organomet. Chem., 29 (1971) 79; (k) K. Tamao, T. Nakajima and M. Kumata, Organometallics, 3 (1984) 1655; (l) L.R. Robinson, G.T. Burns and T.J. Barton, J. Am. Chem. Soc., 107 (1985) 3935; (m) G. Märkl, M. Horn and W. Schlosser, Tetrahedron Lett., 27 (1986) 4019; (n) L. Shui, M.S. Thesis, Louisiana State University, 1987; (o) S.G. Cho, F.K. Cartledge. R.J. Unwalla and S. Profeta, Jr., Tetrahedron, 46 (1990) 8005; (p) S.G. Cho, Bull. Korean Chem. Soc., 13 (1994) 183.
22. For the Lewis acid-catalyzed rearrangement, see: (a) F.C. Whitmore, L.H. Sommer and J. Gold, J. Am. Chem. Soc., 69 (1949) 1976; (b) L.H. Sommer, D.L. Bailey, J.R. Gould and F.C. Whitemore, J. Am. Chem. Soc., 76 (1954) 801; (c) M. Kumada, J.-I. Nakajima, M. Ishikawa and Y. Yamamoto, J. Org. Chem., 23 (1958) 292; (d) M. Kumada and M. Ishikawa, J. Organomet. Chem., 1 (1964) 411; (e) M. Kumada, M. Ishikawa, S. Maeda and K. Ikura. J. Organomet. Chem., 2 (1964) 146; (f) A.G. Brook, K.H. Pannell, G.E. LeGrow and J.J. Sheeto, J. Organomet. Chem., 2 (1964) 491; (g) R.W. Bott, C. Eaborn and B.M. Rushton, J. Organomet. Chem., 3 (1965) 455; (h) O.W. Steward, W.J. Unl and B.W. Sands, J. Organomet. Chem., 15 (1968) 329; (i) W.I. Beven, R.N. Haszeldine, J. Middleton and A.E. Tipping, J. Organomet. Chem., 23 (1970) C17; (j) T.J. Hairston and D.H. O'Brien, J. Organomet. Chem., 29 (1971) 79; (k) K. Tamao, T. Nakajima and M. Kumata, Organometallics, 3 (1984) 1655; (l) L.R. Robinson, G.T. Burns and T.J. Barton, J. Am. Chem. Soc., 107 (1985) 3935; (m) G. Märkl, M. Horn and W. Schlosser, Tetrahedron Lett., 27 (1986) 4019; (n) L. Shui, M.S. Thesis, Louisiana State University, 1987; (o) S.G. Cho, F.K. Cartledge. R.J. Unwalla and S. Profeta, Jr., Tetrahedron, 46 (1990) 8005; (p) S.G. Cho, Bull. Korean Chem. Soc., 13 (1994) 183.
23. For the Lewis acid-catalyzed rearrangement, see: (a) F.C. Whitmore, L.H. Sommer and J. Gold, J. Am. Chem. Soc., 69 (1949) 1976; (b) L.H. Sommer, D.L. Bailey, J.R. Gould and F.C. Whitemore, J. Am. Chem. Soc., 76 (1954) 801; (c) M. Kumada, J.-I. Nakajima, M. Ishikawa and Y. Yamamoto, J. Org. Chem., 23 (1958) 292; (d) M. Kumada and M. Ishikawa, J. Organomet. Chem., 1 (1964) 411; (e) M. Kumada, M. Ishikawa, S. Maeda and K. Ikura. J. Organomet. Chem., 2 (1964) 146; (f) A.G. Brook, K.H. Pannell, G.E. LeGrow and J.J. Sheeto, J. Organomet. Chem., 2 (1964) 491; (g) R.W. Bott, C. Eaborn and B.M. Rushton, J. Organomet. Chem., 3 (1965) 455; (h) O.W. Steward, W.J. Unl and B.W. Sands, J. Organomet. Chem., 15 (1968) 329; (i) W.I. Beven, R.N. Haszeldine, J. Middleton and A.E. Tipping, J. Organomet. Chem., 23 (1970) C17; (j) T.J. Hairston and D.H. O'Brien, J. Organomet. Chem., 29 (1971) 79; (k) K. Tamao, T. Nakajima and M. Kumata, Organometallics, 3 (1984) 1655; (l) L.R. Robinson, G.T. Burns and T.J. Barton, J. Am. Chem. Soc., 107 (1985) 3935; (m) G. Märkl, M. Horn and W. Schlosser, Tetrahedron Lett., 27 (1986) 4019; (n) L. Shui, M.S. Thesis, Louisiana State University, 1987; (o) S.G. Cho, F.K. Cartledge. R.J. Unwalla and S. Profeta, Jr., Tetrahedron, 46 (1990) 8005; (p) S.G. Cho, Bull. Korean Chem. Soc., 13 (1994) 183.
24. For the Lewis acid-catalyzed rearrangement, see: (a) F.C. Whitmore, L.H. Sommer and J. Gold, J. Am. Chem. Soc., 69 (1949) 1976; (b) L.H. Sommer, D.L. Bailey, J.R. Gould and F.C. Whitemore, J. Am. Chem. Soc., 76 (1954) 801; (c) M. Kumada, J.-I. Nakajima, M. Ishikawa and Y. Yamamoto, J. Org. Chem., 23 (1958) 292; (d) M. Kumada and M. Ishikawa, J. Organomet. Chem., 1 (1964) 411; (e) M. Kumada, M. Ishikawa, S. Maeda and K. Ikura. J. Organomet. Chem., 2 (1964) 146; (f) A.G. Brook, K.H. Pannell, G.E. LeGrow and J.J. Sheeto, J. Organomet. Chem., 2 (1964) 491; (g) R.W. Bott, C. Eaborn and B.M. Rushton, J. Organomet. Chem., 3 (1965) 455; (h) O.W. Steward, W.J. Unl and B.W. Sands, J. Organomet. Chem., 15 (1968) 329; (i) W.I. Beven, R.N. Haszeldine, J. Middleton and A.E. Tipping, J. Organomet. Chem., 23 (1970) C17; (j) T.J. Hairston and D.H. O'Brien, J. Organomet. Chem., 29 (1971) 79; (k) K. Tamao, T. Nakajima and M. Kumata, Organometallics, 3 (1984) 1655; (l) L.R. Robinson, G.T. Burns and T.J. Barton, J. Am. Chem. Soc., 107 (1985) 3935; (m) G. Märkl, M. Horn and W. Schlosser, Tetrahedron Lett., 27 (1986) 4019; (n) L. Shui, M.S. Thesis, Louisiana State University, 1987; (o) S.G. Cho, F.K. Cartledge. R.J. Unwalla and S. Profeta, Jr., Tetrahedron, 46 (1990) 8005; (p) S.G. Cho, Bull. Korean Chem. Soc., 13 (1994) 183.
25. For the Lewis acid-catalyzed rearrangement, see: (a) F.C. Whitmore, L.H. Sommer and J. Gold, J. Am. Chem. Soc., 69 (1949) 1976; (b) L.H. Sommer, D.L. Bailey, J.R. Gould and F.C. Whitemore, J. Am. Chem. Soc., 76 (1954) 801; (c) M. Kumada, J.-I. Nakajima, M. Ishikawa and Y. Yamamoto, J. Org. Chem., 23 (1958) 292; (d) M. Kumada and M. Ishikawa, J. Organomet. Chem., 1 (1964) 411; (e) M. Kumada, M. Ishikawa, S. Maeda and K. Ikura. J. Organomet. Chem., 2 (1964) 146; (f) A.G. Brook, K.H. Pannell, G.E. LeGrow and J.J. Sheeto, J. Organomet. Chem., 2 (1964) 491; (g) R.W. Bott, C. Eaborn and B.M. Rushton, J. Organomet. Chem., 3 (1965) 455; (h) O.W. Steward, W.J. Unl and B.W. Sands, J. Organomet. Chem., 15 (1968) 329; (i) W.I. Beven, R.N. Haszeldine, J. Middleton and A.E. Tipping, J. Organomet. Chem., 23 (1970) C17; (j) T.J. Hairston and D.H. O'Brien, J. Organomet. Chem., 29 (1971) 79; (k) K. Tamao, T. Nakajima and M. Kumata, Organometallics, 3 (1984) 1655; (l) L.R. Robinson, G.T. Burns and T.J. Barton, J. Am. Chem. Soc., 107 (1985) 3935; (m) G. Märkl, M. Horn and W. Schlosser, Tetrahedron Lett., 27 (1986) 4019; (n) L. Shui, M.S. Thesis, Louisiana State University, 1987; (o) S.G. Cho, F.K. Cartledge. R.J. Unwalla and S. Profeta, Jr., Tetrahedron, 46 (1990) 8005; (p) S.G. Cho, Bull. Korean Chem. Soc., 13 (1994) 183.
26. For the Lewis acid-catalyzed rearrangement, see: (a) F.C. Whitmore, L.H. Sommer and J. Gold, J. Am. Chem. Soc., 69 (1949) 1976; (b) L.H. Sommer, D.L. Bailey, J.R. Gould and F.C. Whitemore, J. Am. Chem. Soc., 76 (1954) 801; (c) M. Kumada, J.-I. Nakajima, M. Ishikawa and Y. Yamamoto, J. Org. Chem., 23 (1958) 292; (d) M. Kumada and M. Ishikawa, J. Organomet. Chem., 1 (1964) 411; (e) M. Kumada, M. Ishikawa, S. Maeda and K. Ikura. J. Organomet. Chem., 2 (1964) 146; (f) A.G. Brook, K.H. Pannell, G.E. LeGrow and J.J. Sheeto, J. Organomet. Chem., 2 (1964) 491; (g) R.W. Bott, C. Eaborn and B.M. Rushton, J. Organomet. Chem., 3 (1965) 455; (h) O.W. Steward, W.J. Unl and B.W. Sands, J. Organomet. Chem., 15 (1968) 329; (i) W.I. Beven, R.N. Haszeldine, J. Middleton and A.E. Tipping, J. Organomet. Chem., 23 (1970) C17; (j) T.J. Hairston and D.H. O'Brien, J. Organomet. Chem., 29 (1971) 79; (k) K. Tamao, T. Nakajima and M. Kumata, Organometallics, 3 (1984) 1655; (l) L.R. Robinson, G.T. Burns and T.J. Barton, J. Am. Chem. Soc., 107 (1985) 3935; (m) G. Märkl, M. Horn and W. Schlosser, Tetrahedron Lett., 27 (1986) 4019; (n) L. Shui, M.S. Thesis, Louisiana State University, 1987; (o) S.G. Cho, F.K. Cartledge. R.J. Unwalla and S. Profeta, Jr., Tetrahedron, 46 (1990) 8005; (p) S.G. Cho, Bull. Korean Chem. Soc., 13 (1994) 183.
27. For the rearrangement with nucleophiles, see: (a) C. Eaborn and J.C. Jeffrey, J. Chem. Soc., (1957) 137; (b) L.H. Sommer, W.P. Barie, Jr. and D.R. Weyenberg, J. Am. Chem. Soc., 81 (1959) 251; (c) E.A. Francis and J.Y. Corey, J. Organomet. Chem., 61 (1979) C20; (d) J.Y. Corey and V.H.T. Chang, J. Organomet. Chem., 179 (1979) C15; (e) J.Y. Corey, E.R. Corey, V.H.T. Chang, M.A. Hauser, M.A. Leiber, T.E. Reinsel and M.E. Riva, Organometallics, 3 (1984) 1051. (f) R. Damrauer, S.E. Danahey and V.E. Yost, J. Am. Chem. Soc., 106 (1984) 7633; (g) R.L. Kreeger, P.R. Menard, E.A. Sans and H. Shechter, Tetrahedron Lett., 26 (1985) 1115; (h) E.A. Sans and H. Shechter, Tetrahedron Lett., 26 (1985) 1119; (i) R. Damrauer, V.E. Yost, S.E. Danahey and B. O'Connell, Organometallics, 4 (1985) 1779; (j) R. Tacke and R. Rohe-Aehle, J. Organomet. Chem., 354 (1988) 139.
28. For the rearrangement with nucleophiles, see: (a) C. Eaborn and J.C. Jeffrey, J. Chem. Soc., (1957) 137; (b) L.H. Sommer, W.P. Barie, Jr. and D.R. Weyenberg, J. Am. Chem. Soc., 81 (1959) 251; (c) E.A. Francis and J.Y. Corey, J. Organomet. Chem., 61 (1979) C20; (d) J.Y. Corey and V.H.T. Chang, J. Organomet. Chem., 179 (1979) C15; (e) J.Y. Corey, E.R. Corey, V.H.T. Chang, M.A. Hauser, M.A. Leiber, T.E. Reinsel and M.E. Riva, Organometallics, 3 (1984) 1051. (f) R. Damrauer, S.E. Danahey and V.E. Yost, J. Am. Chem. Soc., 106 (1984) 7633; (g) R.L. Kreeger, P.R. Menard, E.A. Sans and H. Shechter, Tetrahedron Lett., 26 (1985) 1115; (h) E.A. Sans and H. Shechter, Tetrahedron Lett., 26 (1985) 1119; (i) R. Damrauer, V.E. Yost, S.E. Danahey and B. O'Connell, Organometallics, 4 (1985) 1779; (j) R. Tacke and R. Rohe-Aehle, J. Organomet. Chem., 354 (1988) 139.
29. For the rearrangement with nucleophiles, see: (a) C. Eaborn and J.C. Jeffrey, J. Chem. Soc., (1957) 137; (b) L.H. Sommer, W.P. Barie, Jr. and D.R. Weyenberg, J. Am. Chem. Soc., 81 (1959) 251; (c) E.A. Francis and J.Y. Corey, J. Organomet. Chem., 61 (1979) C20; (d) J.Y. Corey and V.H.T. Chang, J. Organomet. Chem., 179 (1979) C15; (e) J.Y. Corey, E.R. Corey, V.H.T. Chang, M.A. Hauser, M.A. Leiber, T.E. Reinsel and M.E. Riva, Organometallics, 3 (1984) 1051. (f) R. Damrauer, S.E. Danahey and V.E. Yost, J. Am. Chem. Soc., 106 (1984) 7633; (g) R.L. Kreeger, P.R. Menard, E.A. Sans and H. Shechter, Tetrahedron Lett., 26 (1985) 1115; (h) E.A. Sans and H. Shechter, Tetrahedron Lett., 26 (1985) 1119; (i) R. Damrauer, V.E. Yost, S.E. Danahey and B. O'Connell, Organometallics, 4 (1985) 1779; (j) R. Tacke and R. Rohe-Aehle, J. Organomet. Chem., 354 (1988) 139.
30. For the rearrangement with nucleophiles, see: (a) C. Eaborn and J.C. Jeffrey, J. Chem. Soc., (1957) 137; (b) L.H. Sommer, W.P. Barie, Jr. and D.R. Weyenberg, J. Am. Chem. Soc., 81 (1959) 251; (c) E.A. Francis and J.Y. Corey, J. Organomet. Chem., 61 (1979) C20; (d) J.Y. Corey and V.H.T. Chang, J. Organomet. Chem., 179 (1979) C15; (e) J.Y. Corey, E.R. Corey, V.H.T. Chang, M.A. Hauser, M.A. Leiber, T.E. Reinsel and M.E. Riva, Organometallics, 3 (1984) 1051. (f) R. Damrauer, S.E. Danahey and V.E. Yost, J. Am. Chem. Soc., 106 (1984) 7633; (g) R.L. Kreeger, P.R. Menard, E.A. Sans and H. Shechter, Tetrahedron Lett., 26 (1985) 1115; (h) E.A. Sans and H. Shechter, Tetrahedron Lett., 26 (1985) 1119; (i) R. Damrauer, V.E. Yost, S.E. Danahey and B. O'Connell, Organometallics, 4 (1985) 1779; (j) R. Tacke and R. Rohe-Aehle, J. Organomet. Chem., 354 (1988) 139.
31. For the rearrangement with nucleophiles, see: (a) C. Eaborn and J.C. Jeffrey, J. Chem. Soc., (1957) 137; (b) L.H. Sommer, W.P. Barie, Jr. and D.R. Weyenberg, J. Am. Chem. Soc., 81 (1959) 251; (c) E.A. Francis and J.Y. Corey, J. Organomet. Chem., 61 (1979) C20; (d) J.Y. Corey and V.H.T. Chang, J. Organomet. Chem., 179 (1979) C15; (e) J.Y. Corey, E.R. Corey, V.H.T. Chang, M.A. Hauser, M.A. Leiber, T.E. Reinsel and M.E. Riva, Organometallics, 3 (1984) 1051. (f) R. Damrauer, S.E. Danahey and V.E. Yost, J. Am. Chem. Soc., 106 (1984) 7633; (g) R.L. Kreeger, P.R. Menard, E.A. Sans and H. Shechter, Tetrahedron Lett., 26 (1985) 1115; (h) E.A. Sans and H. Shechter, Tetrahedron Lett., 26 (1985) 1119; (i) R. Damrauer, V.E. Yost, S.E. Danahey and B. O'Connell, Organometallics, 4 (1985) 1779; (j) R. Tacke and R. Rohe-Aehle, J. Organomet. Chem., 354 (1988) 139.
32. For the rearrangement with nucleophiles, see: (a) C. Eaborn and J.C. Jeffrey, J. Chem. Soc., (1957) 137; (b) L.H. Sommer, W.P. Barie, Jr. and D.R. Weyenberg, J. Am. Chem. Soc., 81 (1959) 251; (c) E.A. Francis and J.Y. Corey, J. Organomet. Chem., 61 (1979) C20; (d) J.Y. Corey and V.H.T. Chang, J. Organomet. Chem., 179 (1979) C15; (e) J.Y. Corey, E.R. Corey, V.H.T. Chang, M.A. Hauser, M.A. Leiber, T.E. Reinsel and M.E. Riva, Organometallics, 3 (1984) 1051. (f) R. Damrauer, S.E. Danahey and V.E. Yost, J. Am. Chem. Soc., 106 (1984) 7633; (g) R.L. Kreeger, P.R. Menard, E.A. Sans and H. Shechter, Tetrahedron Lett., 26 (1985) 1115; (h) E.A. Sans and H. Shechter, Tetrahedron Lett., 26 (1985) 1119; (i) R. Damrauer, V.E. Yost, S.E. Danahey and B. O'Connell, Organometallics, 4 (1985) 1779; (j) R. Tacke and R. Rohe-Aehle, J. Organomet. Chem., 354 (1988) 139.
33. For the rearrangement with nucleophiles, see: (a) C. Eaborn and J.C. Jeffrey, J. Chem. Soc., (1957) 137; (b) L.H. Sommer, W.P. Barie, Jr. and D.R. Weyenberg, J. Am. Chem. Soc., 81 (1959) 251; (c) E.A. Francis and J.Y. Corey, J. Organomet. Chem., 61 (1979) C20; (d) J.Y. Corey and V.H.T. Chang, J. Organomet. Chem., 179 (1979) C15; (e) J.Y. Corey, E.R. Corey, V.H.T. Chang, M.A. Hauser, M.A. Leiber, T.E. Reinsel and M.E. Riva, Organometallics, 3 (1984) 1051. (f) R. Damrauer, S.E. Danahey and V.E. Yost, J. Am. Chem. Soc., 106 (1984) 7633; (g) R.L. Kreeger, P.R. Menard, E.A. Sans and H. Shechter, Tetrahedron Lett., 26 (1985) 1115; (h) E.A. Sans and H. Shechter, Tetrahedron Lett., 26 (1985) 1119; (i) R. Damrauer, V.E. Yost, S.E. Danahey and B. O'Connell, Organometallics, 4 (1985) 1779; (j) R. Tacke and R. Rohe-Aehle, J. Organomet. Chem., 354 (1988) 139.
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