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33947300410
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Kochi, J.K.1
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0000866416
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(a) Newcomb, M.; Glenn, A. G.; Williams, W. G. J. Org. Chem. 1989, 54, 2675-2681.
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Glenn, A.G.2
Williams, W.G.3
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7
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0029840673
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(c) Newcomb, M.; Tanaka, N.; Bouvier, A.; Tronche, C.; Horner, J. H.; Musa, O. M.; Martinez, F. N. J. Am. Chem. Soc. 1996, 118, 8505-8506.
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Tanaka, N.2
Bouvier, A.3
Tronche, C.4
Horner, J.H.5
Musa, O.M.6
Martinez, F.N.7
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8
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0027538424
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For an excellent introduction to kinetic analysis of such systems see: Newcomb, M. Tetrahedron 1993, 49, 1151-1176.
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Newcomb, M.1
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0001014264
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(c) Martin-Esker, A. A.; Johnson, C. C.; Horner, J. H.; Newcomb, M. J. Am. Chem. Soc. 1994, 116, 9174-9181.
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Martin-Esker, A.A.1
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17
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0000994935
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(a) Martinez, F. N.; Schlegel, H. B.; Newcomb, M. J. Org. Chem. 1998, 63, 3618-3623.
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Martinez, F.N.1
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18
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0000494887
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(b) Martinez, F. N.; Schlegel, H. B.; Newcomb, M. J. Org. Chem. 1996, 61, 8547-8550.
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Martinez, F.N.1
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Newcomb, M.3
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21
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0000315424
-
Radical Cyclizations and Sequential Radical Reactions
-
Trost, B. M., Ed.; Permagon; Oxford, Chapter 4.2
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(b) Curran, D. P. Radical Cyclizations and Sequential Radical Reactions. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Permagon; Oxford, 1991; Vol. 4, Chapter 4.2, pp 779-831.
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, vol.4
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Curran, D.P.1
-
24
-
-
37049081509
-
-
2 is used to generate a ketyl radical adjacent to a cyclopropyl ring, see Batey, R. A.; Motherwell, W. B. Tetrahedron Lett. 1991, 32, 6649-6652.
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(1992)
J. Chem. Soc., Chem. Commun.
, pp. 942-944
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Batey, R.A.1
Grice, P.2
Harling, J.D.3
Motherwell, W.B.4
Rzepa, H.S.5
-
25
-
-
0001608244
-
-
2 is used to generate a ketyl radical adjacent to a cyclopropyl ring, see Batey, R. A.; Motherwell, W. B. Tetrahedron Lett. 1991, 32, 6649-6652.
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(1991)
J. Org. Chem.
, vol.56
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Clive, D.L.J.1
Daigneault, S.2
-
26
-
-
0006940816
-
-
2 is used to generate a ketyl radical adjacent to a cyclopropyl ring, see Batey, R. A.; Motherwell, W. B. Tetrahedron Lett. 1991, 32, 6649-6652.
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(1972)
J. Org. Chem.
, vol.37
, pp. 2546-2550
-
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Friedrich, E.C.1
Holmstead, R.L.2
-
27
-
-
0001733006
-
-
2 is used to generate a ketyl radical adjacent to a cyclopropyl ring, see Batey, R. A.; Motherwell, W. B. Tetrahedron Lett. 1991, 32, 6649-6652.
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(1972)
J. Org. Chem.
, vol.37
, pp. 2550-2554
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Friedrich, E.C.1
Holmstead, R.L.2
-
28
-
-
0026782705
-
-
2 is used to generate a ketyl radical adjacent to a cyclopropyl ring, see Batey, R. A.; Motherwell, W. B. Tetrahedron Lett. 1991, 32, 6649-6652.
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(1992)
Tetrahedron
, vol.48
, pp. 8031-8052
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Batey, R.A.1
Harling, J.D.2
Motherwell, W.B.3
-
30
-
-
0010619539
-
-
2 is used to generate a ketyl radical adjacent to a cyclopropyl ring, see Batey, R. A.; Motherwell, W. B. Tetrahedron Lett. 1991, 32, 6649-6652.
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(1976)
J. Chem. Soc., Perk. Trans. 2
, pp. 1719-1724
-
-
Davies, A.G.1
Muggleton, B.2
Godet, J.-Y.3
Pereyre, M.4
Pommier, J.-C.5
-
32
-
-
0000022107
-
-
2 is used to generate a ketyl radical adjacent to a cyclopropyl ring, see Batey, R. A.; Motherwell, W. B. Tetrahedron Lett. 1991, 32, 6649-6652.
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(1991)
J. Org. Chem.
, vol.56
, pp. 5285-5289
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Clive, D.L.J.1
Daigneault, S.2
-
33
-
-
0344071458
-
-
2 is used to generate a ketyl radical adjacent to a cyclopropyl ring, see Batey, R. A.; Motherwell, W. B. Tetrahedron Lett. 1991, 32, 6649-6652.
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(1973)
J. Org. Chem.
, vol.38
, pp. 112-116
-
-
Thies, R.W.1
McRitchie, D.D.2
-
34
-
-
0026015020
-
-
2 is used to generate a ketyl radical adjacent to a cyclopropyl ring, see Batey, R. A.; Motherwell, W. B. Tetrahedron Lett. 1991, 32, 6649-6652.
-
(1991)
Tetrahedron Lett.
, vol.32
, pp. 6649-6652
-
-
Batey, R.A.1
Motherwell, W.B.2
-
36
-
-
0344071456
-
-
The yield of the ring-expanded product typically is 0-10% in these cases; however, exceptions have been reported: see refs 10a and 13c
-
The yield of the ring-expanded product typically is 0-10% in these cases; however, exceptions have been reported: see refs 10a and 13c.
-
-
-
-
43
-
-
0000691402
-
-
A system similar to 3 has been reported: Dauben, W. G.; Shatter, G. W.; Deviny, E. J. J. Am. Chem. Soc. 1970, 92, 6273-6281. Here, photoexcitation of I led to the ring-expanded 1-acetylcycloheptene (II), but under the conditions of the experiment, the product isolated was primarily the dimerized material. figure presented
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(1970)
J. Am. Chem. Soc.
, vol.92
, pp. 6273-6281
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Dauben, W.G.1
Shatter, G.W.2
Deviny, E.J.3
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44
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0032559994
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Kantorowski, E. J.; Borhan, B.; Nazarian, S.; Kurth, M. J. Tetrahedron Lett. 1998, 39, 2483-2486.
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, vol.39
, pp. 2483-2486
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Kantorowski, E.J.1
Borhan, B.2
Nazarian, S.3
Kurth, M.J.4
-
45
-
-
11644264856
-
-
Barton, D. H. R.; Crich, D.; Motherwell, W. B. Tetrahedron 1985, 41, 3901-3924.
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(1985)
Tetrahedron
, vol.41
, pp. 3901-3924
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Barton, D.H.R.1
Crich, D.2
Motherwell, W.B.3
-
47
-
-
0026590430
-
-
(a) Takahashi, H.; Yoshioka, M.; Ohno, M.; Kobayashi, S. Tetrahedron Lett. 1992, 33, 2575-2578.
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(1992)
Tetrahedron Lett.
, vol.33
, pp. 2575-2578
-
-
Takahashi, H.1
Yoshioka, M.2
Ohno, M.3
Kobayashi, S.4
-
48
-
-
0030932220
-
-
(b) McDonald, W. S.; Verbicky, C. A.; Zercher, C. K. J. Org. Chem. 1997, 62, 1215-1222.
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, vol.62
, pp. 1215-1222
-
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McDonald, W.S.1
Verbicky, C.A.2
Zercher, C.K.3
-
49
-
-
0345364975
-
-
Also confirmed by TLC analysis
-
Also confirmed by TLC analysis.
-
-
-
-
50
-
-
33845183210
-
-
Franz, J. A.; Bushaw, B. A.; Alnajjar, M. S. J. Am. Chem. Soc. 1989, 111, 268-275.
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J. Am. Chem. Soc.
, vol.111
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-
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Franz, J.A.1
Bushaw, B.A.2
Alnajjar, M.S.3
-
51
-
-
0000087095
-
-
The cyclopropylcarbinyl radical substructure of 3, due to a resonance component which provides additional stabilization, may not react at a rate equal to that of n-butyl radical. For a commentary, see footnote 12 in Newcomb, M.; Glenn, A. G. J. Am. Chem. Soc. 1989, 111, 275-277.
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(1989)
J. Am. Chem. Soc.
, vol.111
, pp. 275-277
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Newcomb, M.1
Glenn, A.G.2
-
53
-
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0001360724
-
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Johnston, L. J.; Lusztyk, J.; Wayner, D. D. M.; Abeywickreyma, A. N.; Beckwith, A. L. J.; Scaiano, J. C.; Ingold, K. U. J. Am. Chem. Soc. 1985, 107, 4594-4596.
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Johnston, L.J.1
Lusztyk, J.2
Wayner, D.D.M.3
Abeywickreyma, A.N.4
Beckwith, A.L.J.5
Scaiano, J.C.6
Ingold, K.U.7
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55
-
-
0025914098
-
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Majetich, G.; Song, J.-S.; Ringold, C.; Nemeth, G. A.; Newton, M. G. J. Org. Chem. 1991, 56, 3973-3988.
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Majetich, G.1
Song, J.-S.2
Ringold, C.3
Nemeth, G.A.4
Newton, M.G.5
-
56
-
-
33847799798
-
-
Ireland, R. E.; Mueller, R. H.; Willard, A. K. J. Am. Chem. Soc. 1976, 98, 2868-2877.
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J. Am. Chem. Soc.
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Ireland, R.E.1
Mueller, R.H.2
Willard, A.K.3
-
58
-
-
0000662936
-
-
(b) de Meijere, A. Angew. Chem., Int. Ed. Engl. 1979, 18, 8, 809-826.
-
(1979)
Angew. Chem., Int. Ed. Engl.
, vol.18
, Issue.8
, pp. 809-826
-
-
Meijere, A.1
-
60
-
-
0345318268
-
-
Although the term σ-bond will generally be used in this discussion in reference to the cyclopropyl skeletal bonds, it is generally acknowledged that these bonds actually incorporate p- as well as s-character
-
Although the term σ-bond will generally be used in this discussion in reference to the cyclopropyl skeletal bonds, it is generally acknowledged that these bonds actually incorporate p- as well as s-character.
-
-
-
-
61
-
-
0345318269
-
-
An alternative view presents itself in the realization that the orbitals which combine to form the cyclopropane σ-bonds have a high degree of p-character, thereby affording good p-p overlap with the radical p-orbital
-
An alternative view presents itself in the realization that the orbitals which combine to form the cyclopropane σ-bonds have a high degree of p-character, thereby affording good p-p overlap with the radical p-orbital.
-
-
-
-
62
-
-
0345318267
-
-
Other factors, assuredly, can modify this ideal situation
-
Other factors, assuredly, can modify this ideal situation.
-
-
-
-
63
-
-
0344455325
-
-
note
-
Though it has been previously suggested for relatively simple systems that build-up of negative charge at the forming radical center in the transition state kinetically favors the primary radical product over the secondary (see ref 2b), our calculations indicate a partial positive charge on the incipient secondary radical center on TS4 which, regardless of steric effects discussed later, should be stabilized by its secondary nature.
-
-
-
-
64
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0344024138
-
-
Biosym Technologies Inc. 9685 Scranton Rd., San Diego, CA 92121-2777
-
InsightII ver 3.2.0 Biosym Technologies Inc. 9685 Scranton Rd., San Diego, CA 92121-2777.
-
InsightII Ver 3.2.0
-
-
-
65
-
-
0344024137
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-
G Wave function Inc. 18401 Von Karman Suite 370, Irvine, CA 92715
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Spartan SGI version 3.1.2 G Wave function Inc. 18401 Von Karman Suite 370, Irvine, CA 92715
-
Spartan SGI Version 3.1.2
-
-
-
66
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-
0004133516
-
-
Gaussian, Inc., Pittsburgh, PA
-
(a) Frisch, M. J.; Trucks, G. W.; Head-Gordon, M.; Gill, P. M. W.; Wong, M. W.; Foresman, J. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M. A.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. Gaussian 92, Revision A. Gaussian, Inc., Pittsburgh, PA, 1992.
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(1992)
Gaussian 92, Revision A
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Frisch, M.J.1
Trucks, G.W.2
Head-Gordon, M.3
Gill, P.M.W.4
Wong, M.W.5
Foresman, J.B.6
Johnson, B.G.7
Schlegel, H.B.8
Robb, M.A.9
Replogle, E.S.10
Gomperts, R.11
Andres, J.L.12
Raghavachari, K.13
Binkley, J.S.14
Gonzalez, C.15
Martin, R.L.16
Fox, D.J.17
Defrees, D.J.18
Baker, J.19
Stewart, J.J.P.20
Pople, J.A.21
more..
-
67
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-
0004133516
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-
Gaussian, Inc. Pittsburgh, PA
-
(b) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94. Gaussian, Inc. Pittsburgh, PA, 1995.
-
(1995)
Gaussian 94
-
-
Frisch, M.J.1
Trucks, G.W.2
Schlegel, H.B.3
Gill, P.M.W.4
Johnson, B.5
Montgomery, J.A.6
Raghavachari, K.7
Al-Laham, M.A.8
Zakrzewski, V.G.9
Challacombe, M.10
Peng, C.Y.11
Ayala, P.Y.12
Chen, W.13
Wong, M.W.14
Andres, J.L.15
Replogle, E.S.16
Gomperts, R.17
Martin, R.L.18
Fox, D.J.19
Binkley, J.S.20
Defrees, D.J.21
Baker, J.22
Stewart, J.P.23
Head-Gordon, M.24
Gonzalez, C.25
Pople, J.A.26
more..
-
68
-
-
0344887092
-
-
note
-
-1.
-
-
-
-
69
-
-
0344887091
-
-
All zero point energies used in calculating the reported zero point corrected energy values have been subjected to the standard 0.89 frequency scaling factor
-
All zero point energies used in calculating the reported zero point corrected energy values have been subjected to the standard 0.89 frequency scaling factor.
-
-
-
-
70
-
-
0345318266
-
-
2 hybridized in the product
-
2 hybridized in the product.
-
-
-
-
71
-
-
0344024134
-
-
note
-
Ab initio calculation results in other cyclopropylcarbinyl radical systems indicate that though these calculations prove quite useful for relative barrier height comparisons, absolute barrier heights should be viewed with some caution (see ref 6a).
-
-
-
-
73
-
-
0344024133
-
-
One should not discount the destabilizing effect on TS6 of the partial adoption of the twist-boat conformation
-
One should not discount the destabilizing effect on TS6 of the partial adoption of the twist-boat conformation.
-
-
-
-
75
-
-
33947483256
-
-
From bond dissociation energies: Benson, S. W. J. Chem. Educ. 1965, 42, 502-518.
-
(1965)
J. Chem. Educ.
, vol.42
, pp. 502-518
-
-
Benson, S.W.1
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