-
3
-
-
0041338323
-
-
Barton, D., Ollis, W. D., Eds.; Pergamon Press: New York
-
(a) Wakefield, B. J. In Comprehensive Organic Chemistry; Barton, D., Ollis, W. D., Eds.; Pergamon Press: New York, 1979; Vol. 3, pp 944, 974-6.
-
(1979)
Comprehensive Organic Chemistry
, vol.3
, pp. 944
-
-
Wakefield, B.J.1
-
4
-
-
0042841052
-
-
Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York
-
(b) Wardell, J. L.; Lindsell, W. E. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 1, pp 52-4 and 156-78, respectively.
-
(1982)
Comprehensive Organometallic Chemistry
, vol.1
, pp. 52-54
-
-
Wardell, J.L.1
Lindsell, W.E.2
-
8
-
-
0031051853
-
-
(d) Garst, J. F.; Ungvary, F.; Baxter, J. T. J. Am. Chem. Soc. 1997, 119, 253.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 253
-
-
Garst, J.F.1
Ungvary, F.2
Baxter, J.T.3
-
9
-
-
0000827420
-
-
(e) Garst, J. F.; Deutch, J. E.; Whitesides, G. M. J. Am. Chem. Soc. 1986, 108, 2490.
-
(1986)
J. Am. Chem. Soc.
, vol.108
, pp. 2490
-
-
Garst, J.F.1
Deutch, J.E.2
Whitesides, G.M.3
-
11
-
-
85069280453
-
-
Reference 3a,b
-
(b) Reference 3a,b.
-
-
-
-
12
-
-
0026565216
-
-
and references therein
-
(c) Walborsky, H. M.; Ollman, J.; Hamdouchi, C.; Topolski, M. Tetrahedron Lett. 1992, 33, 761 and references therein.
-
(1992)
Tetrahedron Lett.
, vol.33
, pp. 761
-
-
Walborsky, H.M.1
Ollman, J.2
Hamdouchi, C.3
Topolski, M.4
-
13
-
-
33847086363
-
-
(a) Rogers, H. R.; Hill, C. L.; Fugiwara, Y.; Rogers, R. J.; Mitchell, H. L.; Whitesides, G. M. J. Am. Chem. Soc. 1980, 102, 217.
-
(1980)
J. Am. Chem. Soc.
, vol.102
, pp. 217
-
-
Rogers, H.R.1
Hill, C.L.2
Fugiwara, Y.3
Rogers, R.J.4
Mitchell, H.L.5
Whitesides, G.M.6
-
14
-
-
0011087605
-
-
(b) Rogers, H. R.; Deutch, J.; Whitesides, G. M. J. Am. Chem. Soc. 1980, 102, 226.
-
(1980)
J. Am. Chem. Soc.
, vol.102
, pp. 226
-
-
Rogers, H.R.1
Deutch, J.2
Whitesides, G.M.3
-
15
-
-
0007241964
-
-
(c) Rogers, H. R.; Rogers, R. J.; Mitchell, H. L.; Whitesides, G. M. J. Am. Chem. Soc. 1980, 102, 231.
-
(1980)
J. Am. Chem. Soc.
, vol.102
, pp. 231
-
-
Rogers, H.R.1
Rogers, R.J.2
Mitchell, H.L.3
Whitesides, G.M.4
-
17
-
-
0032554107
-
-
(a) Curran, D. P.; Lin, C.-H.; DeMello, N.; Junggebauer, J. J. Am. Chem. Soc. 1998, 120, 342.
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 342
-
-
Curran, D.P.1
Lin, C.-H.2
DeMello, N.3
Junggebauer, J.4
-
18
-
-
33748225421
-
-
(b) Sibi, M. P.; Ji, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 190.
-
(1996)
Angew. Chem., Int. Ed. Engl.
, vol.35
, pp. 190
-
-
Sibi, M.P.1
Ji, J.2
-
19
-
-
0001176666
-
-
(c) Curran, D. P.; Qi, H.; DeMello, N. C.; Lin, C.-H. J. Am. Chem. Soc. 1994, 116, 8430.
-
(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 8430
-
-
Curran, D.P.1
Qi, H.2
DeMello, N.C.3
Lin, C.-H.4
-
22
-
-
78249239915
-
-
Frankland, E. Ann. 1849, 71, 171.
-
(1849)
Ann.
, vol.71
, pp. 171
-
-
Frankland, E.1
-
23
-
-
0032537674
-
-
For a recent review, see: (a) Knochel P.; Almena-Perea J. J.; Jones P. Tetrahedron 1998, 54, 8275. For some articles, see: (b) Rieke, R. D.; Hanson, M. V.; Brown, J. D. J. Org. Chem. 1996, 61, 2726. (c) Chen, T.-A.; Wu, X.; Rieke, R. D. J. Am. Chem. Sac. 1995, 117, 233. (d) Hanson, M. V.; Rieke, R. D. J. Am. Chem. Soc. 1995, 117, 10775.
-
(1998)
Tetrahedron
, vol.54
, pp. 8275
-
-
Knochel, P.1
Almena-Perea, J.J.2
Jones, P.3
-
24
-
-
0000618905
-
-
For a recent review, see: (a) Knochel P.; Almena-Perea J. J.; Jones P. Tetrahedron 1998, 54, 8275. For some articles, see: (b) Rieke, R. D.; Hanson, M. V.; Brown, J. D. J. Org. Chem. 1996, 61, 2726. (c) Chen, T.-A.; Wu, X.; Rieke, R. D. J. Am. Chem. Sac. 1995, 117, 233. (d) Hanson, M. V.; Rieke, R. D. J. Am. Chem. Soc. 1995, 117, 10775.
-
(1996)
J. Org. Chem.
, vol.61
, pp. 2726
-
-
Rieke, R.D.1
Hanson, M.V.2
Brown, J.D.3
-
25
-
-
0001714999
-
-
For a recent review, see: (a) Knochel P.; Almena-Perea J. J.; Jones P. Tetrahedron 1998, 54, 8275. For some articles, see: (b) Rieke, R. D.; Hanson, M. V.; Brown, J. D. J. Org. Chem. 1996, 61, 2726. (c) Chen, T.-A.; Wu, X.; Rieke, R. D. J. Am. Chem. Sac. 1995, 117, 233. (d) Hanson, M. V.; Rieke, R. D. J. Am. Chem. Soc. 1995, 117, 10775.
-
(1995)
J. Am. Chem. Sac.
, vol.117
, pp. 233
-
-
Chen, T.-A.1
Wu, X.2
Rieke, R.D.3
-
26
-
-
0000080839
-
-
For a recent review, see: (a) Knochel P.; Almena-Perea J. J.; Jones P. Tetrahedron 1998, 54, 8275. For some articles, see: (b) Rieke, R. D.; Hanson, M. V.; Brown, J. D. J. Org. Chem. 1996, 61, 2726. (c) Chen, T.-A.; Wu, X.; Rieke, R. D. J. Am. Chem. Sac. 1995, 117, 233. (d) Hanson, M. V.; Rieke, R. D. J. Am. Chem. Soc. 1995, 117, 10775.
-
(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 10775
-
-
Hanson, M.V.1
Rieke, R.D.2
-
28
-
-
0000591250
-
-
(b) Lipshutz, B. H.; Wood, M. R.; Tirade, R. J. Am. Chem. Soc. 1995, 117, 6126.
-
(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 6126
-
-
Lipshutz, B.H.1
Wood, M.R.2
Tirade, R.3
-
30
-
-
0001602650
-
-
(d) Knochel, P.; Chou, T.-S.; Jubert, C.; Rajagopal, D. J. Org. Chem. 1993, 58, 588.
-
(1993)
J. Org. Chem.
, vol.58
, pp. 588
-
-
Knochel, P.1
Chou, T.-S.2
Jubert, C.3
Rajagopal, D.4
-
32
-
-
85069283772
-
-
Reference 11a
-
(f) Reference 11a.
-
-
-
-
33
-
-
0000358709
-
-
(a) Zhu, L.; Wehmeyer, R. M.; Rieke, R. D. J. Drg. Chem. 1991, 56, 1445.
-
(1991)
J. Drg. Chem.
, vol.56
, pp. 1445
-
-
Zhu, L.1
Wehmeyer, R.M.2
Rieke, R.D.3
-
34
-
-
0000512023
-
-
For earlier forms of Zn* with lower activity, see: (b) Rieke, R. D.; Li, P. T.; Burns, T. P.; Uhm, S. T. J. Org. Chem. 1981, 46, 4323. (c) Rieke, R. D.; Uhm, S. J.; Hudnall, P. M. J. Chem. Soc., Chem. Commun. 1973, 269.
-
(1981)
J. Org. Chem.
, vol.46
, pp. 4323
-
-
Rieke, R.D.1
Li, P.T.2
Burns, T.P.3
Uhm, S.T.4
-
35
-
-
37049138739
-
-
For earlier forms of Zn* with lower activity, see: (b) Rieke, R. D.; Li, P. T.; Burns, T. P.; Uhm, S. T. J. Org. Chem. 1981, 46, 4323. (c) Rieke, R. D.; Uhm, S. J.; Hudnall, P. M. J. Chem. Soc., Chem. Commun. 1973, 269.
-
(1973)
J. Chem. Soc., Chem. Commun.
, pp. 269
-
-
Rieke, R.D.1
Uhm, S.J.2
Hudnall, P.M.3
-
36
-
-
0003625966
-
-
Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York
-
Boersma, J. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 2, p 832.
-
(1982)
Comprehensive Organometallic Chemistry
, vol.2
, pp. 832
-
-
Boersma, J.1
-
37
-
-
0032479487
-
-
Reported at the 217th National Meeting of the American Chemical Society, Anaheim, CA, March 1999. For a preliminary communication, see: Guijarro, A.; Rieke, R. D. Angew. Chem., Int. Ed. Engl. 1998, 37, 1679.
-
(1998)
Angew. Chem., Int. Ed. Engl.
, vol.37
, pp. 1679
-
-
Guijarro, A.1
Rieke, R.D.2
-
38
-
-
85069281870
-
-
Hartley, F. R., Patai, S., Eds.; John Wiley & Sons: Chichester-New York
-
Stille, J. K. In The Chemistry of Metal-Carbon Bond; Hartley, F. R., Patai, S., Eds.; John Wiley & Sons: Chichester-New York, 1985; Vol. 2, pp 629-630.
-
(1985)
The Chemistry of Metal-Carbon Bond
, vol.2
, pp. 629-630
-
-
Stille, J.K.1
-
39
-
-
0344670464
-
-
Yao, C.-Y. Diss. Abstr. 1964, 24, 4414; Chem. Abstr. 1964, 61, 6443g.
-
(1964)
Diss. Abstr.
, vol.24
, pp. 4414
-
-
Yao, C.-Y.1
-
40
-
-
84915490512
-
-
Yao, C.-Y. Diss. Abstr. 1964, 24, 4414; Chem. Abstr. 1964, 61, 6443g.
-
(1964)
Chem. Abstr.
, vol.61
-
-
-
41
-
-
0003911221
-
-
Cornell University Press: London
-
Rehybridization of the carbon in the transition state releases strain in cyclopentyl derivatives: Brown, H. C. Boranes in Organic Chemistry; Cornell University Press: London, 1972; pp 105-107, 126-128. In 1-adamantyl derivatives the situation is opposite, due to the rigidity of the backbone.
-
(1972)
Boranes in Organic Chemistry
, pp. 105-107
-
-
Brown, H.C.1
-
42
-
-
0004105856
-
-
Longman Scientific & Technical: Harlow Essex, England
-
-. Isaacs, N. S. Physical Organic Chemistry; Longman Scientific & Technical: Harlow Essex, England, 1987; pp 380-381.
-
(1987)
Physical Organic Chemistry
, pp. 380-381
-
-
Isaacs, N.S.1
-
43
-
-
85069279066
-
-
note
-
Intuitively attributed to some degree of nonreproducible thermal decomposition through the stationary phase.
-
-
-
-
46
-
-
0001279377
-
-
(b) Bakac, A.; Butkovic, V.; Espenson, J. H.; Orhanovic, M. Inorg. Chem. 1993, 32, 5886.
-
(1993)
Inorg. Chem.
, vol.32
, pp. 5886
-
-
Bakac, A.1
Butkovic, V.2
Espenson, J.H.3
Orhanovic, M.4
-
47
-
-
85069280939
-
-
Present paper
-
Present paper.
-
-
-
-
48
-
-
0000757786
-
-
Finke, R. G.; Schiraldi, D. A.; Hirose, Y. J. Am. Chem. Soc. 1981, 103, 1876.
-
(1981)
J. Am. Chem. Soc.
, vol.103
, pp. 1876
-
-
Finke, R.G.1
Schiraldi, D.A.2
Hirose, Y.3
-
51
-
-
0003666126
-
-
From ref 19. Original paper: Fox, R. J.; Evans, F. W.; Szwarc, M. Trans. Faraday Soc. 1961, 57, 1915.
-
(1961)
Trans. Faraday Soc.
, vol.57
, pp. 1915
-
-
Fox, R.J.1
Evans, F.W.2
Szwarc, M.3
-
52
-
-
33845374004
-
-
Andrieux, C. P.; Gallardo, I.; Savéant, J.-M.; Su, K.-B. J. Am. Chem. Soc. 1986, 108, 638.
-
(1986)
J. Am. Chem. Soc.
, vol.108
, pp. 638
-
-
Andrieux, C.P.1
Gallardo, I.2
Savéant, J.-M.3
Su, K.-B.4
-
53
-
-
84918127727
-
-
Patai, S., Ed.; John Wiley & Sons: London-New York
-
(a) Casanova, J.; Eberson, L. In The Chemistry of the Carbon-Halogen Bond; Patai, S., Ed.; John Wiley & Sons: London-New York, 1973; Part 2, pp 979-1047.
-
(1973)
The Chemistry of the Carbon-Halogen Bond
, Issue.2 PART
, pp. 979-1047
-
-
Casanova, J.1
Eberson, L.2
-
56
-
-
0032506574
-
-
Velarde-Ortiz, R.; Guijarro, A.; Rieke, R. D. Tetrahedron Lett. 1998, 39, 9157.
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 9157
-
-
Velarde-Ortiz, R.1
Guijarro, A.2
Rieke, R.D.3
-
57
-
-
0000744779
-
-
Evans, D. A.; Britton T. C.; Dorow, R. L.; Dellaria, J. F. Tetrahedron 1988, 44, 5525.
-
(1988)
Tetrahedron
, vol.44
, pp. 5525
-
-
Evans, D.A.1
Britton, T.C.2
Dorow, R.L.3
Dellaria, J.F.4
-
59
-
-
0010640653
-
-
(a) Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543.
-
(1969)
J. Org. Chem.
, vol.34
, pp. 2543
-
-
Dale, J.A.1
Dull, D.L.2
Mosher, H.S.3
-
60
-
-
33947086629
-
-
(b) Sullivan, G. R.; Dale, J. A.; Mosher, H. S. J. Org. Chem. 1973, 38, 2143.
-
(1973)
J. Org. Chem.
, vol.38
, pp. 2143
-
-
Sullivan, G.R.1
Dale, J.A.2
Mosher, H.S.3
-
61
-
-
0006598563
-
-
Radicals on the carbon have been proposed in the reaction of Grignard reagents with oxygen: Lamb, R. C.; Ayers, P. W.; Toney, M. K.; Garst, J. F. J. Am. Chem. Soc. 1966, 88, 4261.
-
(1966)
J. Am. Chem. Soc.
, vol.88
, pp. 4261
-
-
Lamb, R.C.1
Ayers, P.W.2
Toney, M.K.3
Garst, J.F.4
-
63
-
-
0030935084
-
-
Micounin, L.; Oestreich, M.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1997, 36, 245.
-
(1997)
Angew. Chem., Int. Ed. Engl.
, vol.36
, pp. 245
-
-
Micounin, L.1
Oestreich, M.2
Knochel, P.3
-
64
-
-
0001500051
-
-
N2 equilibration such as exo- and endo-7-iodonorearane were found to react with complete loss of their stereochemical integrity: Duddu, R.; Eckhardt, M.; Furlong, M.; Knoess, P.; Berger, S.; Knochel, P. Tetrahedron 1994, 50, 2415. This and the evidence accumulated in this work point to a radical-induced loss of stereochemistry, rather than retention in the reduction step.
-
(1988)
Tetrahedron Lett.
, vol.29
, pp. 5373
-
-
Luche, J.L.1
Allavena, C.2
Petrier, C.3
Dupuy, C.4
-
65
-
-
0344881536
-
-
N2 equilibration such as exo- and endo-7-iodonorearane were found to react with complete loss of their stereochemical integrity: Duddu, R.; Eckhardt, M.; Furlong, M.; Knoess, P.; Berger, S.; Knochel, P. Tetrahedron 1994, 50, 2415. This and the evidence accumulated in this work point to a radical-induced loss of stereochemistry, rather than retention in the reduction step.
-
(1983)
J. Org. Chem.
, vol.48
, pp. 2233
-
-
Turecek, F.1
Veres, K.2
Kocovsky, P.3
Pouzar, V.4
Fajkos, J.5
-
66
-
-
0028032063
-
-
N2 equilibration such as exo- and endo-7-iodonorearane were found to react with complete loss of their stereochemical integrity: Duddu, R.; Eckhardt, M.; Furlong, M.; Knoess, P.; Berger, S.; Knochel, P. Tetrahedron 1994, 50, 2415. This and the evidence accumulated in this work point to a radical-induced loss of stereochemistry, rather than retention in the reduction step.
-
(1994)
Tetrahedron
, vol.50
, pp. 2415
-
-
Duddu, R.1
Eckhardt, M.2
Furlong, M.3
Knoess, P.4
Berger, S.5
Knochel, P.6
-
69
-
-
0000574358
-
-
(b) Samat, A.; Vacher, B.; Chanon, M. J. Org. Chem. 1991, 56, 3524.
-
(1991)
J. Org. Chem.
, vol.56
, pp. 3524
-
-
Samat, A.1
Vacher, B.2
Chanon, M.3
-
70
-
-
0001178666
-
-
(a) Meyer, C.; Marek, I., Courtemanche, G.; Normant, J.-F. Synlett 1993, 266.
-
(1993)
Synlett
, pp. 266
-
-
Meyer, C.1
Marek, I.2
Courtemanche, G.3
Normant, J.-F.4
-
71
-
-
0027485540
-
-
(b) Meyer, C.; Marek, I.; Courtemanche, G.; Normant, J.-F. Tetrahedron Lett. 1993, 34, 6053.
-
(1993)
Tetrahedron Lett.
, vol.34
, pp. 6053
-
-
Meyer, C.1
Marek, I.2
Courtemanche, G.3
Normant, J.-F.4
-
73
-
-
0001437849
-
-
(b) Bowry, V. W.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc. 1991, 113, 5687.
-
(1991)
J. Am. Chem. Soc.
, vol.113
, pp. 5687
-
-
Bowry, V.W.1
Lusztyk, J.2
Ingold, K.U.3
-
74
-
-
85069277992
-
-
note
-
No cyclopentanone could be detected by GLC analysis of the hydrolyzed (2 M HCl) crude reaction mixture.
-
-
-
-
75
-
-
0345101282
-
-
Very unstable Zn(I) complexes have been produced by pulse radiolysis of solutions of Zn(II) complexes: Weddel, J. K.; Allred, A. L.; Meyerstein, D. J. Inorg. Nucl. Chem. 1980, 42, 219.
-
(1980)
J. Inorg. Nucl. Chem.
, vol.42
, pp. 219
-
-
Weddel, J.K.1
Allred, A.L.2
Meyerstein, D.3
-
79
-
-
85069277323
-
-
note
-
Alignment of the C-X dipole to the potential field gradient near the surface might induce ionization of the bond. This mechanism, suggested in electrochemical reductions, was later discarded: ref 27a, pp 1016-1018.
-
-
-
-
80
-
-
85069282276
-
-
note
-
Bridgehead bicyclic halides, among others, would be expected to be far less reactive: ref 27a, pp 1017-1018.
-
-
-
-
81
-
-
0029789547
-
-
(a) Sastry, G. N.; Danovich, D,; Shaik, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1098.
-
(1996)
Angew. Chem., Int. Ed. Engl.
, vol.35
, pp. 1098
-
-
Sastry, G.N.1
Danovich, D.2
Shaik, S.3
-
82
-
-
33748215321
-
-
(b) Fawcett, W. R.; Opallo, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 2131.
-
(1994)
Angew. Chem., Int. Ed. Engl.
, vol.33
, pp. 2131
-
-
Fawcett, W.R.1
Opallo, M.2
-
83
-
-
0000847947
-
-
(a) Bertran, J.; Gallardo, I.; Moreno, M.; Savéant, J.-M. J. Am. Chem. Soc. 1992, 114, 9576.
-
(1992)
J. Am. Chem. Soc.
, vol.114
, pp. 9576
-
-
Bertran, J.1
Gallardo, I.2
Moreno, M.3
Savéant, J.-M.4
-
85
-
-
85069280260
-
-
Reference 36, Chapter viii
-
(c) Reference 36, Chapter viii.
-
-
-
-
86
-
-
0002439767
-
-
(d) Grimshaw, J.; Langan, J. R.; Salmon, G. A. J. Chem. Soc., Faraday Trans. I 1994, 90, 75.
-
(1994)
J. Chem. Soc., Faraday Trans. I
, vol.90
, pp. 75
-
-
Grimshaw, J.1
Langan, J.R.2
Salmon, G.A.3
-
87
-
-
33847085663
-
-
(a) Andrieux, C. P.; Blocman, C.; Dumas-Bouchiat, J.-M.; M'Halla, F.; Savéant, J.-M. J. Am. Chem. Soc. 1980, 102, 3806.
-
(1980)
J. Am. Chem. Soc.
, vol.102
, pp. 3806
-
-
Andrieux, C.P.1
Blocman, C.2
Dumas-Bouchiat, J.-M.3
M'Halla, F.4
Savéant, J.-M.5
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88
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-
0000025927
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(b) Andrieux, C. P.; Blocman, C.; Dumas-Bouchiat, J.-M.; Savéant, J.-M. J. Am. Chem. Soc. 1979, 101, 3432.
-
(1979)
J. Am. Chem. Soc.
, vol.101
, pp. 3432
-
-
Andrieux, C.P.1
Blocman, C.2
Dumas-Bouchiat, J.-M.3
Savéant, J.-M.4
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89
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85069283930
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-
Reference 36, pp 122-123
-
(c) Reference 36, pp 122-123.
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-
-
-
96
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-
0000165414
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-
For example, the Marcus theory for outer-sphere ET was applied to alkyl halide reductions by inner- and outer-sphere reagents with reasonable success: Eberson, L. Acta Chem. Scand. 1982, B36, 533.
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(1982)
Acta Chem. Scand.
, vol.B36
, pp. 533
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-
Eberson, L.1
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97
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85069283343
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-
note
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p(n-RBr).
-
-
-
-
100
-
-
85069275013
-
-
note
-
3 ↔ ...] were used to describe the transition state: ref 56.
-
-
-
-
101
-
-
85069283075
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-
note
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(b) An outer-sphere ET cannot be totally ruled out: ref 6d.
-
-
-
-
102
-
-
85012331749
-
-
•, is an irreversible step. An equilibrium seems reasonable for this step. Indeed, ΔH is only slightly exothermic in these halogen transfers: Nash, G. A.; Skinner, H. A.; Stack, W. F. Trans. Faraday Soc. 1965, 61, 640, 2122. This would explain why this reaction is abnormally positioned toward the right in Figure 2.
-
(1968)
J. Am. Chem. Soc.
, vol.90
, pp. 7047
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Carlsson, D.J.1
Ingold, K.U.2
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103
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0040976087
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-
•, is an irreversible step. An equilibrium seems reasonable for this step. Indeed, ΔH is only slightly exothermic in these halogen transfers: Nash, G. A.; Skinner, H. A.; Stack, W. F. Trans. Faraday Soc. 1965, 61, 640, 2122. This would explain why this reaction is abnormally positioned toward the right in Figure 2.
-
(1965)
Trans. Faraday Soc.
, vol.61
, pp. 640
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Nash, G.A.1
Skinner, H.A.2
Stack, W.F.3
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108
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33845185612
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(a) Andrieux, C. P.; Gallardo, I.; Savéant, J.-M. J. Am. Chem. Soc. 1989, 111, 1620.
-
(1989)
J. Am. Chem. Soc.
, vol.111
, pp. 1620
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-
Andrieux, C.P.1
Gallardo, I.2
Savéant, J.-M.3
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109
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85069276143
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Reference 26
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(b) Reference 26.
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-
-
-
110
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85069276492
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Reference 37, Chapter vii
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Reference 37, Chapter vii.
-
-
-
-
112
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0004032955
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-
John Wiley & Sons: New York
-
"The formations of Grignard reagents and organolithium compounds are examples of the reduction of alkyl halides directly by metals.... It is not clear whether inner- or outer-sphere processes are involved since the reactions occurring on a metal surface offer only a limited number of probes": Kochi, J. K. Free Radicals: John Wiley & Sons: New York, 1973; 663.
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(1973)
Free Radicals
, pp. 663
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Kochi, J.K.1
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113
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85069278331
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-
note
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rel plot for both reactions being a measure of the relative selectivity.
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-
-
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114
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0003625968
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Wilkinson, G., Ed.; Pergamon Press: Oxford-New York
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(a) Prince, R. H. In Comprehensive Coordination Chemistry; Wilkinson, G., Ed.; Pergamon Press: Oxford-New York, 1987; Vol. 5, pp 983-985.
-
(1987)
Comprehensive Coordination Chemistry
, vol.5
, pp. 983-985
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Prince, R.H.1
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116
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0003730993
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McGraw-Hill: New York
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σ values; (a) Hine, J. Physical Organic Chemistry; McGraw-Hill: New York, 1962. (b) Isaacs, N. S. Physical Organic Chemistry; Longman Scientific & Technical: Harlow Essex, England, 1987.
-
(1962)
Physical Organic Chemistry
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Hine, J.1
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117
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0004105856
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Longman Scientific & Technical: Harlow Essex, England
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σ values; (a) Hine, J. Physical Organic Chemistry; McGraw-Hill: New York, 1962. (b) Isaacs, N. S. Physical Organic Chemistry; Longman Scientific & Technical: Harlow Essex, England, 1987.
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(1987)
Physical Organic Chemistry
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Isaacs, N.S.1
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118
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85069280515
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note
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Calculated from kinetic data in ref 6c.
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-
-
-
120
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0007819366
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Sease, J. W.; Burton, F. G.; Nickol, S. L. J. Am. Chem. Soc. 1968, 90, 2595.
-
(1968)
J. Am. Chem. Soc.
, vol.90
, pp. 2595
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Sease, J.W.1
Burton, F.G.2
Nickol, S.L.3
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123
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85069280957
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Chapman, N. B., Shorter, J., Eds.; Plenum Press: London-New York
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Chipperfield, J. R. In Advances in Linear Free Energy Relationships; Chapman, N. B., Shorter, J., Eds.; Plenum Press: London-New York, 1972; p 340.
-
(1972)
Advances in Linear Free Energy Relationships
, pp. 340
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Chipperfield, J.R.1
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124
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0001313287
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-
Studies of tin hydride reductions of bridgehead aliphatic halides have been interpretated as indicating little or no charge separation in the transition state: Fort, R. C., Jr.; Hiti, J. J. Org. Chem. 1977, 42, 3968. However, positive slope of the Hammett plot, ρ = 1.4 points toward some participation of ET with partial negative charge generation at the transition state.
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(1977)
J. Org. Chem.
, vol.42
, pp. 3968
-
-
Fort R.C., Jr.1
Hiti, J.2
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125
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85069276785
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-
note
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Electrochemical reductions have been referred to as "compulsory ET processes" and for inert smooth Pt and some C electrodes is assumed to be outer-sphere ET. For a dropping Hg electrode, which is the case considered here, the situation has been discussed: ref 37, p 79.
-
-
-
-
126
-
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85069275664
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-
note
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With some restrictions, see Table 6, footnote g.
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-
-
-
128
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-
84987453860
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-
N2 for primary bromides and ET for hindered systems: Zhou, D.-L.; Walder, P.; Scheffold, R.; Walder, L. Helv. Chim. Acta 1992, 75, 995.
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(1992)
Helv. Chim. Acta
, vol.75
, pp. 995
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Zhou, D.-L.1
Walder, P.2
Scheffold, R.3
Walder, L.4
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130
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0026093516
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Grinberg, S.; Shaubi, E. Tetrahedron 1991, 47, 2895. The crude reaction mixture was distilled under vacuum, and an intermediate fraction (61% p-isomer/39% o-isomer) was used in the reaction with active zinc.
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(1991)
Tetrahedron
, vol.47
, pp. 2895
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-
Grinberg, S.1
Shaubi, E.2
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131
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85069281366
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-
note
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The steady-state approximation, applied to eq 4, gave, without the aid of a computer, a reasonable estimate of the distribution of products. Nonetheless, to compare with experimental results, exact numbers were preferred.
-
-
-
-
132
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85069281948
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-
note
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2 ≥ 135 would be required to yield 96% of 9a.
-
-
-
-
134
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0017093218
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-
Bestmann, H. J.; Vostrowsky, O.; Stransky, W. Chem. Ber. 1976, 109, 3375.
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(1976)
Chem. Ber.
, vol.109
, pp. 3375
-
-
Bestmann, H.J.1
Vostrowsky, O.2
Stransky, W.3
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