-
2
-
-
0001451085
-
-
(b) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177.
-
(1996)
Chem. Rev.
, vol.96
, pp. 177
-
-
Ryu, I.1
Sonoda, N.2
Curran, D.P.3
-
3
-
-
0011204990
-
-
(a) Bashir, N.; Patro, B.; Murphy, J. A. Adv. Free Radical Chem. 1999, 2, 123.
-
(1999)
Adv. Free Radical Chem.
, vol.2
, pp. 123
-
-
Bashir, N.1
Patro, B.2
Murphy, J.A.3
-
4
-
-
0038800178
-
-
Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim
-
(b) Murphy, J. A. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 1, p 298.
-
(2001)
Radicals in Organic Synthesis
, vol.1
, pp. 298
-
-
Murphy, J.A.1
-
5
-
-
0002025512
-
-
Mattay, J., Ed.; Springer: Berlin
-
(a) Hintz, S.; Heidbreder, A.; Mattay, J. In Topics in Current Chemistry; Mattay, J., Ed.; Springer: Berlin, 1996; Vol. 177, p 77.
-
(1996)
Topics in Current Chemistry
, vol.177
, pp. 77
-
-
Hintz, S.1
Heidbreder, A.2
Mattay, J.3
-
6
-
-
0344901362
-
-
(b) Bauld, N. L.; Bellville, D. J.; Harirchian, B.; Lorenz, K. T.; Pabon, R. A.; Reynolds, D. W.; Wirth, D. D.; Chiou, H.-S.; Marsh, B. K. Acc. Chem. Res. 1987, 20, 371.
-
(1987)
Acc. Chem. Res.
, vol.20
, pp. 371
-
-
Bauld, N.L.1
Bellville, D.J.2
Harirchian, B.3
Lorenz, K.T.4
Pabon, R.A.5
Reynolds, D.W.6
Wirth, D.D.7
Chiou, H.-S.8
Marsh, B.K.9
-
7
-
-
0031573815
-
-
(c) Schmittel, M.; Burghart, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 2550.
-
(1997)
Angew. Chem., Int. Ed. Engl.
, vol.36
, pp. 2550
-
-
Schmittel, M.1
Burghart, A.2
-
8
-
-
0037189905
-
-
Of course, it is certainly possible to take advantage of this second oxidation as illustrated by Moeller's recent synthesis of nemorensic acid: Liu, B.; Duan, S.; Sutterer, A. C.; Moeller, K. D. J. Am. Chem. Soc. 2002, 124, 10101.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 10101
-
-
Liu, B.1
Duan, S.2
Sutterer, A.C.3
Moeller, K.D.4
-
9
-
-
37049141009
-
-
Gilbert, B. C.; Larkin, J. P.; Norman, R. O. C. J. Chem. Soc., Perkin Trans. 2 1972, 794.
-
(1972)
J. Chem. Soc., Perkin Trans. 2
, pp. 794
-
-
Gilbert, B.C.1
Larkin, J.P.2
Norman, R.O.C.3
-
11
-
-
0000262774
-
-
Lett, J. T., Adler, H., Eds.; Academic Press: New York
-
(b) von Sonntag, C.; Hagen, U.; Schon-Bopp, A.; Schulte-Frohlinde, D. In Advances in Radiation Biology; Lett, J. T., Adler, H., Eds.; Academic Press: New York, 1981; Vol. 9, p 109.
-
(1981)
Advances in Radiation Biology
, vol.9
, pp. 109
-
-
Von Sonntag, C.1
Hagen, U.2
Schon-Bopp, A.3
Schulte-Frohlinde, D.4
-
12
-
-
0000697108
-
-
(a) Beckwith, A. L. J.; Crich, D.; Duggan, P. J.; Yao, Q. Chem. Rev. 1997, 97, 3273.
-
(1997)
Chem. Rev.
, vol.97
, pp. 3273
-
-
Beckwith, A.L.J.1
Crich, D.2
Duggan, P.J.3
Yao, Q.4
-
13
-
-
0030929539
-
-
(b) Gugger, A.; Batra, R.; Rzadek, P.; Rist, G.; Giese, B. J. Am. Chem. Soc. 1997, 119, 8740.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 8740
-
-
Gugger, A.1
Batra, R.2
Rzadek, P.3
Rist, G.4
Giese, B.5
-
14
-
-
0033564989
-
-
(a) Whitted, P. O.; Homer, J. H.; Newcomb, M.; Huang, X.; Crich, D. Org. Lett. 1999, 1, 153.
-
(1999)
Org. Lett.
, vol.1
, pp. 153
-
-
Whitted, P.O.1
Homer, J.H.2
Newcomb, M.3
Huang, X.4
Crich, D.5
-
15
-
-
0033601068
-
-
(b) Newcomb, M.; Homer, J. H.; Whitted, P. O.; Crich, D.; Huang, X.; Yao, Q.; Zipse, H. J. Am. Chem. Soc. 1999, 121, 10685.
-
(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 10685
-
-
Newcomb, M.1
Homer, J.H.2
Whitted, P.O.3
Crich, D.4
Huang, X.5
Yao, Q.6
Zipse, H.7
-
16
-
-
37049107755
-
-
The highly delocalized alkene radical cation of 1,1-dimethoxyethene could be observed directly by ESR spectroscopy following generation by a fragmentation approach: Behrens, G.; Bothe, E.; Koltzenberg, G.; Schulte-Frohlinde, D. J. Chem. Soc., Perkin Trans. 2 1980, 883.
-
(1980)
J. Chem. Soc., Perkin Trans. 2
, pp. 883
-
-
Behrens, G.1
Bothe, E.2
Koltzenberg, G.3
Schulte-Frohlinde, D.4
-
18
-
-
0001264344
-
-
(b) Crich, D.; Yao, Q.; Filzen, G. F. J. Am. Chem. Soc. 1995, 117, 11455.
-
(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 11455
-
-
Crich, D.1
Yao, Q.2
Filzen, G.F.3
-
19
-
-
0000962275
-
-
(c) Koch, A.; Lamberth, C.; Wetterich, F.; Giese, B. J. Org. Chem. 1993, 58, 1083.
-
(1993)
J. Org. Chem.
, vol.58
, pp. 1083
-
-
Koch, A.1
Lamberth, C.2
Wetterich, F.3
Giese, B.4
-
20
-
-
0001271574
-
-
Renaud, P., Sibi, M., Eds.; Wiley-VCH: Weinheim
-
(d) Crich, D. In Radicals in Organic Synthesis; Renaud, P., Sibi, M., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 2, p 188.
-
(2001)
Radicals in Organic Synthesis
, vol.2
, pp. 188
-
-
Crich, D.1
-
23
-
-
0038800128
-
-
A closely related scheme was also advanced earlier by Sprecher: Sprecher, M. Chemtracts: Org. Chem. 1994, 7, 115.
-
(1994)
Chemtracts: Org. Chem.
, vol.7
, pp. 115
-
-
Sprecher, M.1
-
26
-
-
0000782249
-
-
Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim
-
(c) Newcomb, M. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 1, p 317.
-
(2001)
Radicals in Organic Synthesis
, vol.1
, pp. 317
-
-
Newcomb, M.1
-
27
-
-
0000506428
-
-
(a) Koltzenburg, G.; Behrens, G.; Schulte-Frohlinde, D. J. Am. Chem. Soc. 1982, 104, 7311.
-
(1982)
J. Am. Chem. Soc.
, vol.104
, pp. 7311
-
-
Koltzenburg, G.1
Behrens, G.2
Schulte-Frohlinde, D.3
-
28
-
-
0030856922
-
-
(b) Cozens, F. L.; O'Neill, M.; Bogdanova, R.; Schepp, N. J. Am. Chem. Soc. 1997, 119, 10652.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 10652
-
-
Cozens, F.L.1
O'Neill, M.2
Bogdanova, R.3
Schepp, N.4
-
29
-
-
0037093876
-
-
(c) Homer, J. H.; Taxil, E.; Newcomb, M. J. Am. Chem. Soc. 2002, 124, 5402.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 5402
-
-
Homer, J.H.1
Taxil, E.2
Newcomb, M.3
-
34
-
-
0033106113
-
-
(b) Choi, S.-Y.; Crich, D.; Homer, J. H.; Huang, X.; Newcomb, M.; Whitted, P. O. Tetrahedron 1999, 59, 3317.
-
(1999)
Tetrahedron
, vol.59
, pp. 3317
-
-
Choi, S.-Y.1
Crich, D.2
Homer, J.H.3
Huang, X.4
Newcomb, M.5
Whitted, P.O.6
-
35
-
-
0642337274
-
-
For example, time-resolved LFP studies of alkene radical cations generated according to Scheme 3 using a nanosecond laser only detect the diffusively free radical cation and so are unable to provide data on the rates of formation of contact ion pairs or of their trapping. This situation arises because diffusion out of the contact ion pair is expected to be faster than the nanosecond time scale of the instrument: Arnold, B. R.; Noukakis, D.; Farid, S.; Goodman, J. L.; Gould, I. R. J. Am. Chem. Soc. 1995, 117, 4399. For a discussion, see ref 14c.
-
(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 4399
-
-
Arnold, B.R.1
Noukakis, D.2
Farid, S.3
Goodman, J.L.4
Gould, I.R.5
-
36
-
-
0038462375
-
-
note
-
-1 in acetonitrile (both at 20 °C).
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-
-
-
37
-
-
33747565073
-
-
For the use of allyl alcohol as a probe for alkene radical cations, see: Giese, B.; Beyrich-Graf, X.; Burger, J.; Kesselheim, C.; Senn, M.; Schafer, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1742.
-
(1993)
Angew. Chem., Int. Ed. Engl.
, vol.32
, pp. 1742
-
-
Giese, B.1
Beyrich-Graf, X.2
Burger, J.3
Kesselheim, C.4
Senn, M.5
Schafer, T.6
-
38
-
-
0038800135
-
-
note
-
-1.
-
-
-
-
39
-
-
15844425960
-
-
Neutral aminyl radicals are insufficiently electrophilic to achieve rapid intramolecular hydrogen abstraction: Musa, O. M.; Homer, J. H.; Shahin, H.; Newcomb, M. J. Am. Chem. Soc. 1996, 118, 3862.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 3862
-
-
Musa, O.M.1
Homer, J.H.2
Shahin, H.3
Newcomb, M.4
-
40
-
-
0000885140
-
-
(a) Ono, N.; Miyake, H.; Kamimura, A.; Hamamoto, I.; Tamura, R.; Kaji, A. Tetrahedron 1985, 41, 4013.
-
(1985)
Tetrahedron
, vol.41
, pp. 4013
-
-
Ono, N.1
Miyake, H.2
Kamimura, A.3
Hamamoto, I.4
Tamura, R.5
Kaji, A.6
-
42
-
-
0038462370
-
-
note
-
1H NMR spectrum, which facilitates interpretation of spectra of crude reaction mixtures.
-
-
-
-
43
-
-
0034723342
-
-
Crich, D.; Huang, X.; Newcomb, M. J. Org. Chem. 2000, 65, 523.
-
(2000)
J. Org. Chem.
, vol.65
, pp. 523
-
-
Crich, D.1
Huang, X.2
Newcomb, M.3
-
44
-
-
0001186406
-
-
For preliminary communications, see: (a) Crich, D.; Ranganathan, K.; Huang, X. Org. Lett. 2001, 3, 1917.
-
(2001)
Org. Lett.
, vol.3
, pp. 1917
-
-
Crich, D.1
Ranganathan, K.2
Huang, X.3
-
47
-
-
0034674450
-
-
(b) Taber, D. F.; Wang, Y.; Pahutski, T. F. J. Org. Chem. 2000, 65, 3861.
-
(2000)
J. Org. Chem.
, vol.65
, pp. 3861
-
-
Taber, D.F.1
Wang, Y.2
Pahutski, T.F.3
-
49
-
-
0032792653
-
-
It should be noted that Zipse has considered substitutions closely related to the ones employed here as concerted displacements accelerated by the adjacent radical rather than as dissociative mechanisms. The balance of the experimental evidence, however, favors the dissociative pathway, and the computations continue to move in this direction with each successive cycle of refinement: Zipse, H. Acc. Chem. Res. 1999, 32, 571.
-
(1999)
Acc. Chem. Res.
, vol.32
, pp. 571
-
-
Zipse, H.1
-
50
-
-
0020355934
-
-
For a related, rare, example of the cyclization of a 3-allylcyclohexyl radical leading to the formation of the bicyclo[3.2.1]octane type skeleton, see: Hart, D. J.; Tsai, Y. M. J. Org. Chem. 1982, 47, 4403.
-
(1982)
J. Org. Chem.
, vol.47
, pp. 4403
-
-
Hart, D.J.1
Tsai, Y.M.2
-
51
-
-
0001465266
-
-
Brossi, A., Ed.; Academic Press: San Diego
-
Martin, S. F. In The Alkaloids; Brossi, A., Ed.; Academic Press: San Diego, 1987; Vol. 30, p 252.
-
(1987)
The Alkaloids
, vol.30
, pp. 252
-
-
Martin, S.F.1
-
52
-
-
0035943269
-
-
Kobayashi, J.; Hirasawa, Y.; Yoshida, N.; Morita, H. J. Am. Chem. Soc. 2001, 123, 5901.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 5901
-
-
Kobayashi, J.1
Hirasawa, Y.2
Yoshida, N.3
Morita, H.4
-
53
-
-
15144344046
-
-
Sauerberg, P.; Jeppesen, L.; Olesen, P. H.; Rasmussen, T.; Swedberg, M. D. B.; Sheardown, M. J.; Fink-Jensen, A.; Thomsen, C.; Thogersen, H.; Rimvall, K.; Ward, J. S.; Calligaro, D. O.; Delapp, N. W.; Bymaster, F. P.; Shannon, H. E. J. Med. Chem. 1998, 41, 4378.
-
(1998)
J. Med. Chem.
, vol.41
, pp. 4378
-
-
Sauerberg, P.1
Jeppesen, L.2
Olesen, P.H.3
Rasmussen, T.4
Swedberg, M.D.B.5
Sheardown, M.J.6
Fink-Jensen, A.7
Thomsen, C.8
Thogersen, H.9
Rimvall, K.10
Ward, J.S.11
Calligaro, D.O.12
Delapp, N.W.13
Bymaster, F.P.14
Shannon, H.E.15
-
54
-
-
0034618225
-
-
Tamiz, A. P.; Smith, M. P.; Enyedy, I.; Flippen-Anderson, J.; Zhang, M.; Johnson, K. M.; Kozikowski, A. P. Bioorg. Med. Chem. Lett. 2000, 10, 1681.
-
(2000)
Bioorg. Med. Chem. Lett.
, vol.10
, pp. 1681
-
-
Tamiz, A.P.1
Smith, M.P.2
Enyedy, I.3
Flippen-Anderson, J.4
Zhang, M.5
Johnson, K.M.6
Kozikowski, A.P.7
-
55
-
-
0001874067
-
-
O'Brien, R. D., Ed.; Plenum: New York
-
Indeed, Scifinder Scholar locates >2000 substances containing the 1-azabicyclo[3.2.1]octane nucleus with the majority in the medicinal and patent literature, suggesting that this may be an example of a "privileged structure": (a) Ariens, E. J.; Beld, A. J.; Rodrigues de Miranda, J. F.; Simonis, A. M. In The Receptors: A Comprehensive Treatise; O'Brien, R. D., Ed.; Plenum: New York, 1979; Vol. 1, pp 33.
-
(1979)
The Receptors: A Comprehensive Treatise
, vol.1
, pp. 33
-
-
Ariens, E.J.1
Beld, A.J.2
Rodrigues de Miranda, J.F.3
Simonis, A.M.4
-
56
-
-
0024239320
-
-
Indeed, Scifinder Scholar locates >2000 substances containing the 1-azabicyclo[3.2.1]octane nucleus with the majority in the medicinal and patent literature, suggesting that this may be an example of a "privileged structure": (b) Evans, B. E.; Rittle, K. E.; Bock, M. G.; DiPardo, R. M.; Freidinger, R. M.; Whitter, W. L.; Lundell, G. F.; Veber, D. F.; Anderson, P. S.; Chang, R. S. L.; Lotti, V. J.; Cerino, D. J.; Chen, T. B.; Kling, P. J.; Kunkel, K. A.; Springer, J. P.; Hirshfield, J. J. Med. Chem. 1988, 31, 2235.
-
(1988)
J. Med. Chem.
, vol.31
, pp. 2235
-
-
Evans, B.E.1
Rittle, K.E.2
Bock, M.G.3
DiPardo, R.M.4
Freidinger, R.M.5
Whitter, W.L.6
Lundell, G.F.7
Veber, D.F.8
Anderson, P.S.9
Chang, R.S.L.10
Lotti, V.J.11
Cerino, D.J.12
Chen, T.B.13
Kling, P.J.14
Kunkel, K.A.15
Springer, J.P.16
Hirshfield, J.17
-
60
-
-
0013280488
-
-
For the application of related fragmentations in synthesis, see: Aubele, D. L.; Floreancig, P. E. Org. Lett. 2002, 4, 3443.
-
(2002)
Org. Lett.
, vol.4
, pp. 3443
-
-
Aubele, D.L.1
Floreancig, P.E.2
-
61
-
-
0038800177
-
-
note
-
It is interesting to note that, although tributyltin hydride is not soluble in acetonitrile, and indeed partitioning between acetonitrile and hexanes is a favorite method for the removal of organotin byproducts from more polar products, there is sufficient solubility in a hot 1/1 mixture of benzene and acetonitrile for chain reactions to proceed smoothly.
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