Comparative chemistry of η3-oxaallyl and η3-allyl rhodium(I) complexes in the hydrosilylation of cyclopropyl ketones: Observation of an unprecedented rearrangement

Journal of Organometallic Chemistry

Volumn 582, Issue 2, 1999, Pages 235-245

  Sun, Carrie ^a   Tu, Ambrose ^a   Slough, Greg A ^b  

^a CASE WESTERN RESERVE UNIVERSITY   (United States)

^b KALAMAZOO COLLEGE   (United States)

Author keywords

Cyclopropyl carbinyl rearrangement; Kinetics of hydrosilylation; 3 Allyl rhodium; 3 Oxaallyl rhodium

Indexed keywords

EID: 0013198667     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(99)00041-8     Document Type: Article

References (55)

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18. Several homogenous rhodium(I), rhodium(II), platinum(II), copper, and ruthenium(II) complexes efficiently catalyze structural rearrangements of cyclopropane derivatives. (a) J. Halpern, in: I. Wender, P. Pino (Eds.), Organic Syntheses Via Metal Carbonyls, vol. II, Wiley, New York, 1977, p. 705. (b) K.C. Bishop III, Chem. Rev. 76 (1976) 461. (c) S. Sarel, Acc. Chem. Res. 11 (1978) 204. (d) M.P. Doyle, D. van Leusen, J. Org. Chem. 47 (1982) 5326. (e) M. Sohn, J. Blum, J. Am. Chem. Soc. 101 (1979) 2694. (f) J.M. Brown, B.T. Golding, J.J. Stofko Jr., J. Chem. Soc. Perkin Trans. 2 (1978) 436. (g) R.G. Salomon, M.F. Salomon, J.L.C. Kachinski, J. Am. Chem. Soc. 99 (1977) 1043. (h) T.H. Johnson, T.F. Baldwin, J. Org. Chem. 45 (1980) 140. (i) P.G. Gassman, T.J. Atkins, J. Am. Chem. Soc. 94 (1972) 7748. See other examples for catalysis involving strained cyclopropane systems. (j) H.C. Volger, H. Hogeveen, M.M.P. Gaasbeek, J. Am. Chem. Soc. 91 (1969) 2138. (k) H. Hogeveen, H.C. Volger, J. Am. Chem. Soc. 89 (1967) 2486. (l) T.J. Katz, S. Cerefice, J. Am. Chem. Soc. 91 (1969) 2405.
19. Several homogenous rhodium(I), rhodium(II), platinum(II), copper, and ruthenium(II) complexes efficiently catalyze structural rearrangements of cyclopropane derivatives. (a) J. Halpern, in: I. Wender, P. Pino (Eds.), Organic Syntheses Via Metal Carbonyls, vol. II, Wiley, New York, 1977, p. 705. (b) K.C. Bishop III, Chem. Rev. 76 (1976) 461. (c) S. Sarel, Acc. Chem. Res. 11 (1978) 204. (d) M.P. Doyle, D. van Leusen, J. Org. Chem. 47 (1982) 5326. (e) M. Sohn, J. Blum, J. Am. Chem. Soc. 101 (1979) 2694. (f) J.M. Brown, B.T. Golding, J.J. Stofko Jr., J. Chem. Soc. Perkin Trans. 2 (1978) 436. (g) R.G. Salomon, M.F. Salomon, J.L.C. Kachinski, J. Am. Chem. Soc. 99 (1977) 1043. (h) T.H. Johnson, T.F. Baldwin, J. Org. Chem. 45 (1980) 140. (i) P.G. Gassman, T.J. Atkins, J. Am. Chem. Soc. 94 (1972) 7748. See other examples for catalysis involving strained cyclopropane systems. (j) H.C. Volger, H. Hogeveen, M.M.P. Gaasbeek, J. Am. Chem. Soc. 91 (1969) 2138. (k) H. Hogeveen, H.C. Volger, J. Am. Chem. Soc. 89 (1967) 2486. (l) T.J. Katz, S. Cerefice, J. Am. Chem. Soc. 91 (1969) 2405.
20. Several homogenous rhodium(I), rhodium(II), platinum(II), copper, and ruthenium(II) complexes efficiently catalyze structural rearrangements of cyclopropane derivatives. (a) J. Halpern, in: I. Wender, P. Pino (Eds.), Organic Syntheses Via Metal Carbonyls, vol. II, Wiley, New York, 1977, p. 705. (b) K.C. Bishop III, Chem. Rev. 76 (1976) 461. (c) S. Sarel, Acc. Chem. Res. 11 (1978) 204. (d) M.P. Doyle, D. van Leusen, J. Org. Chem. 47 (1982) 5326. (e) M. Sohn, J. Blum, J. Am. Chem. Soc. 101 (1979) 2694. (f) J.M. Brown, B.T. Golding, J.J. Stofko Jr., J. Chem. Soc. Perkin Trans. 2 (1978) 436. (g) R.G. Salomon, M.F. Salomon, J.L.C. Kachinski, J. Am. Chem. Soc. 99 (1977) 1043. (h) T.H. Johnson, T.F. Baldwin, J. Org. Chem. 45 (1980) 140. (i) P.G. Gassman, T.J. Atkins, J. Am. Chem. Soc. 94 (1972) 7748. See other examples for catalysis involving strained cyclopropane systems. (j) H.C. Volger, H. Hogeveen, M.M.P. Gaasbeek, J. Am. Chem. Soc. 91 (1969) 2138. (k) H. Hogeveen, H.C. Volger, J. Am. Chem. Soc. 89 (1967) 2486. (l) T.J. Katz, S. Cerefice, J. Am. Chem. Soc. 91 (1969) 2405.
21. Several homogenous rhodium(I), rhodium(II), platinum(II), copper, and ruthenium(II) complexes efficiently catalyze structural rearrangements of cyclopropane derivatives. (a) J. Halpern, in: I. Wender, P. Pino (Eds.), Organic Syntheses Via Metal Carbonyls, vol. II, Wiley, New York, 1977, p. 705. (b) K.C. Bishop III, Chem. Rev. 76 (1976) 461. (c) S. Sarel, Acc. Chem. Res. 11 (1978) 204. (d) M.P. Doyle, D. van Leusen, J. Org. Chem. 47 (1982) 5326. (e) M. Sohn, J. Blum, J. Am. Chem. Soc. 101 (1979) 2694. (f) J.M. Brown, B.T. Golding, J.J. Stofko Jr., J. Chem. Soc. Perkin Trans. 2 (1978) 436. (g) R.G. Salomon, M.F. Salomon, J.L.C. Kachinski, J. Am. Chem. Soc. 99 (1977) 1043. (h) T.H. Johnson, T.F. Baldwin, J. Org. Chem. 45 (1980) 140. (i) P.G. Gassman, T.J. Atkins, J. Am. Chem. Soc. 94 (1972) 7748. See other examples for catalysis involving strained cyclopropane systems. (j) H.C. Volger, H. Hogeveen, M.M.P. Gaasbeek, J. Am. Chem. Soc. 91 (1969) 2138. (k) H. Hogeveen, H.C. Volger, J. Am. Chem. Soc. 89 (1967) 2486. (l) T.J. Katz, S. Cerefice, J. Am. Chem. Soc. 91 (1969) 2405.
22. Several homogenous rhodium(I), rhodium(II), platinum(II), copper, and ruthenium(II) complexes efficiently catalyze structural rearrangements of cyclopropane derivatives. (a) J. Halpern, in: I. Wender, P. Pino (Eds.), Organic Syntheses Via Metal Carbonyls, vol. II, Wiley, New York, 1977, p. 705. (b) K.C. Bishop III, Chem. Rev. 76 (1976) 461. (c) S. Sarel, Acc. Chem. Res. 11 (1978) 204. (d) M.P. Doyle, D. van Leusen, J. Org. Chem. 47 (1982) 5326. (e) M. Sohn, J. Blum, J. Am. Chem. Soc. 101 (1979) 2694. (f) J.M. Brown, B.T. Golding, J.J. Stofko Jr., J. Chem. Soc. Perkin Trans. 2 (1978) 436. (g) R.G. Salomon, M.F. Salomon, J.L.C. Kachinski, J. Am. Chem. Soc. 99 (1977) 1043. (h) T.H. Johnson, T.F. Baldwin, J. Org. Chem. 45 (1980) 140. (i) P.G. Gassman, T.J. Atkins, J. Am. Chem. Soc. 94 (1972) 7748. See other examples for catalysis involving strained cyclopropane systems. (j) H.C. Volger, H. Hogeveen, M.M.P. Gaasbeek, J. Am. Chem. Soc. 91 (1969) 2138. (k) H. Hogeveen, H.C. Volger, J. Am. Chem. Soc. 89 (1967) 2486. (l) T.J. Katz, S. Cerefice, J. Am. Chem. Soc. 91 (1969) 2405.
23. Several homogenous rhodium(I), rhodium(II), platinum(II), copper, and ruthenium(II) complexes efficiently catalyze structural rearrangements of cyclopropane derivatives. (a) J. Halpern, in: I. Wender, P. Pino (Eds.), Organic Syntheses Via Metal Carbonyls, vol. II, Wiley, New York, 1977, p. 705. (b) K.C. Bishop III, Chem. Rev. 76 (1976) 461. (c) S. Sarel, Acc. Chem. Res. 11 (1978) 204. (d) M.P. Doyle, D. van Leusen, J. Org. Chem. 47 (1982) 5326. (e) M. Sohn, J. Blum, J. Am. Chem. Soc. 101 (1979) 2694. (f) J.M. Brown, B.T. Golding, J.J. Stofko Jr., J. Chem. Soc. Perkin Trans. 2 (1978) 436. (g) R.G. Salomon, M.F. Salomon, J.L.C. Kachinski, J. Am. Chem. Soc. 99 (1977) 1043. (h) T.H. Johnson, T.F. Baldwin, J. Org. Chem. 45 (1980) 140. (i) P.G. Gassman, T.J. Atkins, J. Am. Chem. Soc. 94 (1972) 7748. See other examples for catalysis involving strained cyclopropane systems. (j) H.C. Volger, H. Hogeveen, M.M.P. Gaasbeek, J. Am. Chem. Soc. 91 (1969) 2138. (k) H. Hogeveen, H.C. Volger, J. Am. Chem. Soc. 89 (1967) 2486. (l) T.J. Katz, S. Cerefice, J. Am. Chem. Soc. 91 (1969) 2405.
24. Several homogenous rhodium(I), rhodium(II), platinum(II), copper, and ruthenium(II) complexes efficiently catalyze structural rearrangements of cyclopropane derivatives. (a) J. Halpern, in: I. Wender, P. Pino (Eds.), Organic Syntheses Via Metal Carbonyls, vol. II, Wiley, New York, 1977, p. 705. (b) K.C. Bishop III, Chem. Rev. 76 (1976) 461. (c) S. Sarel, Acc. Chem. Res. 11 (1978) 204. (d) M.P. Doyle, D. van Leusen, J. Org. Chem. 47 (1982) 5326. (e) M. Sohn, J. Blum, J. Am. Chem. Soc. 101 (1979) 2694. (f) J.M. Brown, B.T. Golding, J.J. Stofko Jr., J. Chem. Soc. Perkin Trans. 2 (1978) 436. (g) R.G. Salomon, M.F. Salomon, J.L.C. Kachinski, J. Am. Chem. Soc. 99 (1977) 1043. (h) T.H. Johnson, T.F. Baldwin, J. Org. Chem. 45 (1980) 140. (i) P.G. Gassman, T.J. Atkins, J. Am. Chem. Soc. 94 (1972) 7748. See other examples for catalysis involving strained cyclopropane systems. (j) H.C. Volger, H. Hogeveen, M.M.P. Gaasbeek, J. Am. Chem. Soc. 91 (1969) 2138. (k) H. Hogeveen, H.C. Volger, J. Am. Chem. Soc. 89 (1967) 2486. (l) T.J. Katz, S. Cerefice, J. Am. Chem. Soc. 91 (1969) 2405.
25. Several homogenous rhodium(I), rhodium(II), platinum(II), copper, and ruthenium(II) complexes efficiently catalyze structural rearrangements of cyclopropane derivatives. (a) J. Halpern, in: I. Wender, P. Pino (Eds.), Organic Syntheses Via Metal Carbonyls, vol. II, Wiley, New York, 1977, p. 705. (b) K.C. Bishop III, Chem. Rev. 76 (1976) 461. (c) S. Sarel, Acc. Chem. Res. 11 (1978) 204. (d) M.P. Doyle, D. van Leusen, J. Org. Chem. 47 (1982) 5326. (e) M. Sohn, J. Blum, J. Am. Chem. Soc. 101 (1979) 2694. (f) J.M. Brown, B.T. Golding, J.J. Stofko Jr., J. Chem. Soc. Perkin Trans. 2 (1978) 436. (g) R.G. Salomon, M.F. Salomon, J.L.C. Kachinski, J. Am. Chem. Soc. 99 (1977) 1043. (h) T.H. Johnson, T.F. Baldwin, J. Org. Chem. 45 (1980) 140. (i) P.G. Gassman, T.J. Atkins, J. Am. Chem. Soc. 94 (1972) 7748. See other examples for catalysis involving strained cyclopropane systems. (j) H.C. Volger, H. Hogeveen, M.M.P. Gaasbeek, J. Am. Chem. Soc. 91 (1969) 2138. (k) H. Hogeveen, H.C. Volger, J. Am. Chem. Soc. 89 (1967) 2486. (l) T.J. Katz, S. Cerefice, J. Am. Chem. Soc. 91 (1969) 2405.
26. Several homogenous rhodium(I), rhodium(II), platinum(II), copper, and ruthenium(II) complexes efficiently catalyze structural rearrangements of cyclopropane derivatives. (a) J. Halpern, in: I. Wender, P. Pino (Eds.), Organic Syntheses Via Metal Carbonyls, vol. II, Wiley, New York, 1977, p. 705. (b) K.C. Bishop III, Chem. Rev. 76 (1976) 461. (c) S. Sarel, Acc. Chem. Res. 11 (1978) 204. (d) M.P. Doyle, D. van Leusen, J. Org. Chem. 47 (1982) 5326. (e) M. Sohn, J. Blum, J. Am. Chem. Soc. 101 (1979) 2694. (f) J.M. Brown, B.T. Golding, J.J. Stofko Jr., J. Chem. Soc. Perkin Trans. 2 (1978) 436. (g) R.G. Salomon, M.F. Salomon, J.L.C. Kachinski, J. Am. Chem. Soc. 99 (1977) 1043. (h) T.H. Johnson, T.F. Baldwin, J. Org. Chem. 45 (1980) 140. (i) P.G. Gassman, T.J. Atkins, J. Am. Chem. Soc. 94 (1972) 7748. See other examples for catalysis involving strained cyclopropane systems. (j) H.C. Volger, H. Hogeveen, M.M.P. Gaasbeek, J. Am. Chem. Soc. 91 (1969) 2138. (k) H. Hogeveen, H.C. Volger, J. Am. Chem. Soc. 89 (1967) 2486. (l) T.J. Katz, S. Cerefice, J. Am. Chem. Soc. 91 (1969) 2405.
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