-
1
-
-
33847086035
-
-
Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc. 1980, 102, 2693.
-
(1980)
J. Am. Chem. Soc.
, vol.102
, pp. 2693
-
-
Girard, P.1
Namy, J.L.2
Kagan, H.B.3
-
6
-
-
36749046756
-
-
a) Kagan, H. B.; Namy, J. L.; Girard, P. Tetrahedron 1981, 37, Suppl. 1, 1775.
-
(1981)
Tetrahedron
, vol.37
, Issue.SUPPL. 1
, pp. 1775
-
-
Kagan, H.B.1
Namy, J.L.2
Girard, P.3
-
8
-
-
84989528750
-
-
c) Namy, J. L.; Collin, J.; Bied, C.; Kagan, H. B. Synlett 1992, 733.
-
(1992)
Synlett
, pp. 733
-
-
Namy, J.L.1
Collin, J.2
Bied, C.3
Kagan, H.B.4
-
9
-
-
85022594998
-
-
Mechanistic review: Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943.
-
(1992)
Synlett
, pp. 943
-
-
Curran, D.P.1
Fevig, T.L.2
Jasperse, C.P.3
Totleben, M.J.4
-
12
-
-
0000892265
-
-
c) Murakami, M.; Hayashi, M.; Ito, Y. J. Org. Chem. 1992, 57, 793.
-
(1992)
J. Org. Chem.
, vol.57
, pp. 793
-
-
Murakami, M.1
Hayashi, M.2
Ito, Y.3
-
15
-
-
0000682082
-
-
f) Enholm, E. J.; Xie, Y. P.; Abboud, K. A. J. Org. Chem. 1995, 60, 1112.
-
(1995)
J. Org. Chem.
, vol.60
, pp. 1112
-
-
Enholm, E.J.1
Xie, Y.P.2
Abboud, K.A.3
-
16
-
-
0028930169
-
-
g) Booth, S. E.; Benneche, T.; Undheim, K. Tetrahedron 1995, 51, 3665.
-
(1995)
Tetrahedron
, vol.51
, pp. 3665
-
-
Booth, S.E.1
Benneche, T.2
Undheim, K.3
-
23
-
-
0003242186
-
-
e) Yacovan, A.; Hoz, S.; Bilkis, I. J. Am. Chem. Soc. 1996, 118, 261.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 261
-
-
Yacovan, A.1
Hoz, S.2
Bilkis, I.3
-
27
-
-
0001175715
-
-
Recent references: a) Kan, T.; Nara, S.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5111.
-
(1994)
J. Org. Chem.
, vol.59
, pp. 5111
-
-
Kan, T.1
Nara, S.2
Ito, S.3
Matsuda, F.4
Shirahama, H.5
-
28
-
-
0030069273
-
-
b) Fukuzawa, S.; Furuya, H.; Tsuchimoto, T. Tetrahedron 1996, 52, 1953.
-
(1996)
Tetrahedron
, vol.52
, pp. 1953
-
-
Fukuzawa, S.1
Furuya, H.2
Tsuchimoto, T.3
-
30
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-
0343029297
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note
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We define the terms "Grignard" and "Barbier" based on experimental procedures (eq 1) not mechanisms. In an intramolecular reaction, the halide and ketone are attached, so only the Barbier procedure is possible.
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33
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0001703044
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-
b) For recent measurements of rate constants of reductions of benzyl radicals, see: Skene, W. G.; Scaiano, J. C.; Cozens, F. L. J. Org. Chem. 1996, 61, 7918.
-
(1996)
J. Org. Chem.
, vol.61
, pp. 7918
-
-
Skene, W.G.1
Scaiano, J.C.2
Cozens, F.L.3
-
36
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0343465103
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A similar experiment was performed by Molander and McKie in a bridged system, with similar results (ref. 9b)
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A similar experiment was performed by Molander and McKie in a bridged system, with similar results (ref. 9b).
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-
37
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-
0343743781
-
-
a) Sastry, G. N.; Reddy, A. C.; Shaik, S. Angew. Chem. Int. Ed. Engl. 1995, 34, 34.
-
(1995)
Angew. Chem. Int. Ed. Engl.
, vol.34
, pp. 34
-
-
Sastry, G.N.1
Reddy, A.C.2
Shaik, S.3
-
41
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0342595178
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This assumes that ketyl opening is not reversible
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This assumes that ketyl opening is not reversible.
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42
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0343029293
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note
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The postulate of intramolecular electron transfer suggests that iodoketones might to more reactive than alkyl iodides. The following competition experiment is constant with this suggestion. (Formula Presented)
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43
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0029804421
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However, it is known that Lewis acids can influence the outcome of radical reactions. For recent examples, see a) Sibi, M. P.; Ji, J. G.; Wu, J. H.; Gurtler, S.; Porter, N. A. J. Am. Chem. Soc. 1996, 118, 9200.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 9200
-
-
Sibi, M.P.1
Ji, J.G.2
Wu, J.H.3
Gurtler, S.4
Porter, N.A.5
-
44
-
-
0002535530
-
-
b) Guindon, Y.; Guerin, B.; Rancourt, J.; Chabot, C.; Mackintosh, N.; Ogilvie, W. W. Pure Appl. Chem. 1996, 68, 89.
-
(1996)
Pure Appl. Chem.
, vol.68
, pp. 89
-
-
Guindon, Y.1
Guerin, B.2
Rancourt, J.3
Chabot, C.4
Mackintosh, N.5
Ogilvie, W.W.6
-
45
-
-
0001583170
-
-
c) Renaud, P.; Moufid, N.; Kuo, L. H.; Curran, D. P. J. Org. Chem. 1994, 59, 3547.
-
(1994)
J. Org. Chem.
, vol.59
, pp. 3547
-
-
Renaud, P.1
Moufid, N.2
Kuo, L.H.3
Curran, D.P.4
-
46
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0343029292
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note
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N2-based mechanisms with ketyls, but this type of nucleophilic substitution is supposed to be strongly disfavored with respect to electron transfer. See reference 16.
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47
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0342595177
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2
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2.
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-
-
-
51
-
-
84986413122
-
-
(b) Snowden, R. L.; Brauchli, R.; Sonnay, P. Helv. Chim. Acta. 1989, 72, 570.
-
(1989)
Helv. Chim. Acta.
, vol.72
, pp. 570
-
-
Snowden, R.L.1
Brauchli, R.2
Sonnay, P.3
-
56
-
-
0001434093
-
-
Miura, K.; Ichinose, Y.; Nozaki, K.; Fugami, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1989, 62, 143.
-
(1989)
Bull. Chem. Soc. Jpn.
, vol.62
, pp. 143
-
-
Miura, K.1
Ichinose, Y.2
Nozaki, K.3
Fugami, K.4
Oshima, K.5
Utimoto, K.6
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