-
9
-
-
0009194380
-
-
(a) Moss, R. A.; Dolling, U.-H.; Whittle, J. R. Tetrahedron Lett. 1971, 12, 931.
-
(1971)
Tetrahedron Lett
, vol.12
, pp. 931
-
-
Moss, R.A.1
Dolling, U.-H.2
Whittle, J.R.3
-
13
-
-
0000832153
-
-
(e) Kirmse, W.; Chiem, P. V.; Henning, P. G. J. Am. Chem. Soc. 1983, 105, 1695.
-
(1983)
J. Am. Chem. Soc
, vol.105
, pp. 1695
-
-
Kirmse, W.1
Chiem, P.V.2
Henning, P.G.3
-
20
-
-
51549112272
-
-
Mieusset, J.-L.; Bespokoev, A.; Pacar, M.; Abraham, M.; Arion, V. B.; Brinker, U. H. J. Org. Chem. 2008, 73, 6551.
-
(2008)
J. Org. Chem
, vol.73
, pp. 6551
-
-
Mieusset, J.-L.1
Bespokoev, A.2
Pacar, M.3
Abraham, M.4
Arion, V.B.5
Brinker, U.H.6
-
21
-
-
55049110189
-
-
DOI: 10.1002/ejoc.200800709
-
Mieusset, J.-L.; Billing, P.; Abraham, M.; Arion, V. B.; Brecker, L.; Brinker, U. H. Eur. J. Org. Chem., DOI: 10.1002/ejoc.200800709.
-
Eur. J. Org. Chem
-
-
Mieusset, J.-L.1
Billing, P.2
Abraham, M.3
Arion, V.B.4
Brecker, L.5
Brinker, U.H.6
-
24
-
-
33846211545
-
-
Lecea, B.; Ayerbe, M.; Arrieta, A.; Cossio, F. P.; Branchadell, V.; Ortuño, R. M.; Baceiredo, A. J. Org. Chem. 2007, 72, 357.
-
(2007)
J. Org. Chem
, vol.72
, pp. 357
-
-
Lecea, B.1
Ayerbe, M.2
Arrieta, A.3
Cossio, F.P.4
Branchadell, V.5
Ortuño, R.M.6
Baceiredo, A.7
-
25
-
-
0007405107
-
-
(a) Bernardi, F.; Bottoni, A.; Canepa, C.; Olivucci, M.; Robb, M. A.; Tonachini, G. J. Org. Chem. 1997, 62, 2018.
-
(1997)
J. Org. Chem
, vol.62
, pp. 2018
-
-
Bernardi, F.1
Bottoni, A.2
Canepa, C.3
Olivucci, M.4
Robb, M.A.5
Tonachini, G.6
-
26
-
-
2942588990
-
-
(b) Blavins, J. J.; Cooper, D. L.; Karadakov, P. B. Int. J. Quantum Chem. 2004, 98, 465.
-
(2004)
Int. J. Quantum Chem
, vol.98
, pp. 465
-
-
Blavins, J.J.1
Cooper, D.L.2
Karadakov, P.B.3
-
27
-
-
34250893847
-
-
Wei, H.; Hrovat, D. A.; Dolbier, W. R., Jr.; Smart, B. E.; Borden, W. T. Angew. Chem., Int. Ed. 2007, 46, 2666.
-
(2007)
Angew. Chem., Int. Ed
, vol.46
, pp. 2666
-
-
Wei, H.1
Hrovat, D.A.2
Dolbier Jr., W.R.3
Smart, B.E.4
Borden, W.T.5
-
28
-
-
0033532866
-
-
Krogh-Jespersen, K.; Yan, S.; Moss, R. A. J. Am. Chem. Soc. 1999, 121, 6269.
-
(1999)
J. Am. Chem. Soc
, vol.121
, pp. 6269
-
-
Krogh-Jespersen, K.1
Yan, S.2
Moss, R.A.3
-
29
-
-
0342298223
-
-
Moreno, M.; Lluch, J. M.; Oliva, A.; Bertrán, J. Can. J. Chem. 1987, 65, 2774.
-
(1987)
Can. J. Chem
, vol.65
, pp. 2774
-
-
Moreno, M.1
Lluch, J.M.2
Oliva, A.3
Bertrán, J.4
-
30
-
-
0034992563
-
-
(a) Bühl, M.; Terstegen, F.; Löffler, F.; Meynhardt, B.; Kierse, S.; Müller, M.; Näther, C.; Lüning, U. Eur. J. Org. Chem. 2001, 2151.
-
(2001)
Eur. J. Org. Chem
, pp. 2151
-
-
Bühl, M.1
Terstegen, F.2
Löffler, F.3
Meynhardt, B.4
Kierse, S.5
Müller, M.6
Näther, C.7
Lüning, U.8
-
31
-
-
1242307865
-
-
(b) Fraile, J. M.; García, J. I.; Gil, M. J.; Martínez- Merino, V.; Mayoral, J. A.; Salvatella, L. Chem. Eur. J. 2004, 10, 758.
-
(2004)
Chem. Eur. J
, vol.10
, pp. 758
-
-
Fraile, J.M.1
García, J.I.2
Gil, M.J.3
Martínez- Merino, V.4
Mayoral, J.A.5
Salvatella, L.6
-
32
-
-
0034816899
-
-
(c) Fraile, J. M.; García, J. I.; Martínez-Merino, V.; Mayoral, J. A.; Salvatella, L. J. Am. Chem. Soc. 2001, 123, 7616.
-
(2001)
J. Am. Chem. Soc
, vol.123
, pp. 7616
-
-
Fraile, J.M.1
García, J.I.2
Martínez-Merino, V.3
Mayoral, J.A.4
Salvatella, L.5
-
33
-
-
0037016615
-
-
(d) Rasmussen, T.; Jensen, J. F.; Østergaard, N.; Tanner, D.; Ziegler, T.; Norrby, P.-O. Chem. Eur. J. 2002, 8, 177.
-
(2002)
Chem. Eur. J
, vol.8
, pp. 177
-
-
Rasmussen, T.1
Jensen, J.F.2
Østergaard, N.3
Tanner, D.4
Ziegler, T.5
Norrby, P.-O.6
-
34
-
-
55649103523
-
-
Despite many attempts, we could not find the fourth TS syn to syn, probably because of excessive steric hindrance
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Despite many attempts, we could not find the fourth TS (syn to syn), probably because of excessive steric hindrance.
-
-
-
-
35
-
-
55649107761
-
-
For the purpose of clarity, the usual designations σ, p, π, and π* are used for the description of the orbitals involved in carbene-alkene interactions to present the results of the NBO analysis instead of the notation commonly used by NBO
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For the purpose of clarity, the usual designations σ, p, π, and π* are used for the description of the orbitals involved in carbene-alkene interactions to present the results of the NBO analysis instead of the notation commonly used by NBO. Therefore, LP corresponds to σ, LP* to p, BD(2) to π, and BD*(2) to π*.
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Therefore, LP corresponds to σ, LP* to p, BD(2) to π, and BD*(2) to π*
-
-
-
36
-
-
0033611940
-
-
Keating, A. E.; Merrigan, S. R.; Singleton, D. A.; Houk, K. N. J. Am. Chem. Soc. 1999, 121, 3933.
-
(1999)
J. Am. Chem. Soc
, vol.121
, pp. 3933
-
-
Keating, A.E.1
Merrigan, S.R.2
Singleton, D.A.3
Houk, K.N.4
-
37
-
-
33845551316
-
-
For the utilization of oxadiazolines in carbene chemistry see, for example:a
-
For the utilization of oxadiazolines in carbene chemistry see, for example:(a) Békhazi, M.; Warkentin, J. J. Am. Chem. Soc. 1983, 105, 1289.
-
(1983)
J. Am. Chem. Soc
, vol.105
, pp. 1289
-
-
Békhazi, M.1
Warkentin, J.2
-
38
-
-
0000332197
-
-
(b) Majchrzak, M. W.; Békhazi, M.; Tse-Sheepy, I.; Warkentin, J. J. Org. Chem. 1989, 54, 1842.
-
(1989)
J. Org. Chem
, vol.54
, pp. 1842
-
-
Majchrzak, M.W.1
Békhazi, M.2
Tse-Sheepy, I.3
Warkentin, J.4
-
39
-
-
0000902060
-
-
(c) Tae, E. L.; Zhu, Z.; Platz, M. S.; Pezacki, J. P.; Warkentin, J. J. Phys. Chem. A 1999, 103, 5336.
-
(1999)
J. Phys. Chem. A
, vol.103
, pp. 5336
-
-
Tae, E.L.1
Zhu, Z.2
Platz, M.S.3
Pezacki, J.P.4
Warkentin, J.5
-
41
-
-
27644543491
-
-
(e) Takahashi, Y.; Mori, Y.; Nakamura, A.; Tomioka, H. Tetrahedron Lett. 2005, 46, 8415.
-
(2005)
Tetrahedron Lett
, vol.46
, pp. 8415
-
-
Takahashi, Y.1
Mori, Y.2
Nakamura, A.3
Tomioka, H.4
-
43
-
-
55649092508
-
-
In stabilized carbenes, the p-orbital is already partly filled because of intramolecular electron donation. Therefore, during cyclopropanation, electron density can also flow from the p- to the antibonding π-orbital of the alkene. For norbornenylidene, about three-quarters of the interactions arise from donation of the σ-orbital into the π*-orbital; the rest comes from the p-orbital
-
In stabilized carbenes, the p-orbital is already partly filled because of intramolecular electron donation. Therefore, during cyclopropanation, electron density can also flow from the p- to the antibonding π-orbital of the alkene. For norbornenylidene, about three-quarters of the interactions arise from donation of the σ-orbital into the π*-orbital; the rest comes from the p-orbital.
-
-
-
-
44
-
-
55649097813
-
-
As a carbene, norbornenylidene possesses a significant dipole moment (2.44 D, see the Supporting Information). Therefore, the specific geometry found for the complex is due to an additional stabilization resulting from dipole-dipole interactions which favors an antiparallel orientation of the dipole of the carbene and of the alkene (Supporting Information, p S15). The stabilization is also partly due to dipole-induced dipole interactions (Supporting Information, p S16).
-
As a carbene, norbornenylidene possesses a significant dipole moment (2.44 D, see the Supporting Information). Therefore, the specific geometry found for the complex is due to an additional stabilization resulting from dipole-dipole interactions which favors an antiparallel orientation of the dipole of the carbene and of the alkene (Supporting Information, p S15). The stabilization is also partly due to dipole-induced dipole interactions (Supporting Information, p S16).
-
-
-
-
45
-
-
0000409920
-
-
(a) Turro, N. J.; Lehr, G. F.; Butcher, J. A., Jr.; Moss, R. A.; Guo, W. J. Am. Chem. Soc. 1982, 104, 1754.
-
(1982)
J. Am. Chem. Soc
, vol.104
, pp. 1754
-
-
Turro, N.J.1
Lehr, G.F.2
Butcher Jr., J.A.3
Moss, R.A.4
Guo, W.5
-
46
-
-
0001396769
-
-
(b) Moss, R. A.; Perez, L. A.; Turro, N. J.; Gould, I. R.; Hacker, N. P. Tetrahedron Lett. 1983, 24, 685.
-
(1983)
Tetrahedron Lett
, vol.24
, pp. 685
-
-
Moss, R.A.1
Perez, L.A.2
Turro, N.J.3
Gould, I.R.4
Hacker, N.P.5
-
47
-
-
0000091870
-
-
(c) Eisenthal, K. B.; Moss, R. A.; Turro, N. J. Science 1984, 225, 1439.
-
(1984)
Science
, vol.225
, pp. 1439
-
-
Eisenthal, K.B.1
Moss, R.A.2
Turro, N.J.3
-
48
-
-
0001447626
-
-
(d) Tomioka, H.; Hayashi, N.; Izawa, Y.; Liu, M. T. H. J. Am. Chem. Soc. 1984, 106, 454.
-
(1984)
J. Am. Chem. Soc
, vol.106
, pp. 454
-
-
Tomioka, H.1
Hayashi, N.2
Izawa, Y.3
Liu, M.T.H.4
-
49
-
-
0001586333
-
-
(e) Liu, M. T. H.; Soundararajan, N.; Paike, N.; Subramanian, R. J. Org. Chem. 1987, 52, 4223.
-
(1987)
J. Org. Chem
, vol.52
, pp. 4223
-
-
Liu, M.T.H.1
Soundararajan, N.2
Paike, N.3
Subramanian, R.4
-
51
-
-
0029992211
-
-
(g) Bonneau, R.; Liu, M. T. H.; Kim, K. C.; Goodman, J. L. J. Am. Chem. Soc. 1996, 118, 3829.
-
(1996)
J. Am. Chem. Soc
, vol.118
, pp. 3829
-
-
Bonneau, R.1
Liu, M.T.H.2
Kim, K.C.3
Goodman, J.L.4
-
53
-
-
0001740610
-
-
(b) Houk, K. N.; Rondan, N. G.; Mareda, J. J. Am. Chem. Soc. 1984, 106, 4291.
-
(1984)
J. Am. Chem. Soc
, vol.106
, pp. 4291
-
-
Houk, K.N.1
Rondan, N.G.2
Mareda, J.3
-
54
-
-
0001061763
-
-
(c) Houk, K. N.; Rondan, N. G.; Mareda, J. Tetrahedron 1985, 41, 1555.
-
(1985)
Tetrahedron
, vol.41
, pp. 1555
-
-
Houk, K.N.1
Rondan, N.G.2
Mareda, J.3
-
55
-
-
0039865660
-
-
(d) Blake, J. F.; Wierschke, S. G.; Jorgensen, W. L. J. Am. Chem. Soc. 1989, 111, 1919.
-
(1989)
J. Am. Chem. Soc
, vol.111
, pp. 1919
-
-
Blake, J.F.1
Wierschke, S.G.2
Jorgensen, W.L.3
-
57
-
-
0001440236
-
-
(f) Modarelli, D. A.; Morgan, S.; Platz, M. S. J. Am. Chem. Soc. 1992, 114, 7034.
-
(1992)
J. Am. Chem. Soc
, vol.114
, pp. 7034
-
-
Modarelli, D.A.1
Morgan, S.2
Platz, M.S.3
-
58
-
-
0032547310
-
-
(g) Nigam, M.; Platz, M. S.; Showalter, B. M.; Toscano, J. P.; Johnson, R.; Abbot, S. C.; Kirchhoff, M. M. J. Am. Chem. Soc. 1998, 120, 8055.
-
(1998)
J. Am. Chem. Soc
, vol.120
, pp. 8055
-
-
Nigam, M.1
Platz, M.S.2
Showalter, B.M.3
Toscano, J.P.4
Johnson, R.5
Abbot, S.C.6
Kirchhoff, M.M.7
-
59
-
-
34547899129
-
-
(a) Moss, R. A.; Tian, J.; Sauers, R. R.; Krogh-Jespersen, K. J. Am. Chem. Soc. 2007, 129, 10019.
-
(2007)
J. Am. Chem. Soc
, vol.129
, pp. 10019
-
-
Moss, R.A.1
Tian, J.2
Sauers, R.R.3
Krogh-Jespersen, K.4
-
60
-
-
53349171701
-
-
(b) Moss, R. A.; Wang, L.; Weintraub, E.; Krogh-Jespersen, K. J. Phys. Chem. A 2008, 112, 4651.
-
(2008)
J. Phys. Chem. A
, vol.112
, pp. 4651
-
-
Moss, R.A.1
Wang, L.2
Weintraub, E.3
Krogh-Jespersen, K.4
-
61
-
-
43949136114
-
-
(c) Wang, J.; Kubicki, J.; Peng, H.; Platz, M. S. J. Am. Chem. Soc. 2008, 130, 6604.
-
(2008)
J. Am. Chem. Soc
, vol.130
, pp. 6604
-
-
Wang, J.1
Kubicki, J.2
Peng, H.3
Platz, M.S.4
-
62
-
-
55649090610
-
-
Frisch, M. J.; et al. Gaussian 03; Gaussian, Inc., Pittsburgh, PA, 2003.
-
Frisch, M. J.; et al. Gaussian 03; Gaussian, Inc., Pittsburgh, PA, 2003.
-
-
-
-
64
-
-
0345491105
-
-
Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
-
(1988)
Phys. Rev. B
, vol.37
, pp. 785
-
-
Lee, C.1
Yang, W.2
Parr, R.G.3
|