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0000868520
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2 with 1-hexene provided only 9% of the corresponding bis-selenide adduct on irradiation for 30 h: A. Ogawa, H. Tanaka, H. Yokoyama, R. Obayashi, K. Yokoyama, N. Sonoda, J. Org. Chem. 1992, 57, 111-115.
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Ogawa, A.1
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9
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0002569154
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33845281717
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c) K. Nozaki, K. Oshima, K. Utimoto, J. Am. Chem. Soc. 1987, 109, 2547-2549;
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37049073661
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Kataoka, T.1
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Hori, M.6
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17
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0346524343
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In contrast, α-aryl-substituted vinylic radicals are assumed to be π radicals
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In general, vinyl radicals are believed to be a mixture of stereoisomeric σ radicals, and a fast equilibrium is present between the stereoisomers: a) R. W. Fessenden, R. H. Schuler, J. Chem. Phys. 1963, 39, 2147-2195. In contrast, α-aryl-substituted vinylic radicals are assumed to be π radicals:
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Fessenden, R.W.1
Schuler, R.H.2
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19
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0001304578
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Ethyl propiolate is assumed to generate a vinylic π radical: a) C. Galli, A. Guarnieri, H. Koch, P. Mencarelli, Z. Rappoport, J. Org. Chem. 1997, 62, 4072-4077;
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Rappoport, Z.5
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22
-
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85085674707
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-
note
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+.
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-
-
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26
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33847085176
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d) D. L. J. Clive, G. J. Chittattu, V. Farina, W. A. Kiel, S. M. Menchen, C. G. Russell, A. Singh, C. K. Wong, N. J. Curtis, J. Am. Chem. Soc. 1980, 102, 4438-4447;
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Clive, D.L.J.1
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Menchen, S.M.5
Russell, C.G.6
Singh, A.7
Wong, C.K.8
Curtis, N.J.9
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29
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0001533699
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g) C. Chatgilialoglu, M. Guerra, A. Guerrini, G. Seconi, K. B. Clark, D. Grillen, J. Kanabus-Kaminska, J. A. Martinho-Simòes, J. Org. Chem. 1992, 57, 2427-2433.
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Chatgilialoglu, C.1
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Guerrini, A.3
Seconi, G.4
Clark, K.B.5
Grillen, D.6
Kanabus-Kaminska, J.7
Martinho-Simòes, J.A.8
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32
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0002088557
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H. Okamura, M. Miura, K. Kosugi, H. Takei, Tetrahedron Lett. 1980, 21, 87-90.
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Okamura, H.1
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33
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0000322431
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a) A. Ogawa, Y. Tsuboi, R. Obayashi, K. Yokoyama, I. Ryu, N. Sonoda, J. Org. Chem. 1994, 59, 1600-1601;
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Ogawa, A.1
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Sonoda, N.6
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34
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0347263441
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b) J. V. Comasseto, L. W. Ling, N. Petragnani, H. A. Stefani, Synthesis 1997, 373-403.
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Comasseto, J.V.1
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Stefani, H.A.4
-
35
-
-
0344932372
-
-
note
-
The E/Z ratio of the product reflects that of the vinylic selenide starting material: 5b E/Z = 10/90, 5j E/Z = 7/93, 7b E/Z = 7/93, 7b′ E/Z = 16/84, 7j E/Z = 8/92.
-
-
-
-
36
-
-
85085674713
-
-
note
-
[3a]
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-
-
-
37
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0000315424
-
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(Eds.: B. M. Trost, I. Fleming, M. F. Semmelhock), Pergamon, Oxford
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a) D. P. Curran in Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming, M. F. Semmelhock), Pergamon, Oxford, 1991, pp. 779-831;
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Curran, D.P.1
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38
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85082777144
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b) D. P. Curran, Synthesis 1988, 417-439; D. P. Curran, Synthesis 1988, 489-513;
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Curran, D.P.1
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39
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85064667006
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b) D. P. Curran, Synthesis 1988, 417-439; D. P. Curran, Synthesis 1988, 489-513;
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Synthesis
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Curran, D.P.1
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40
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0004145743
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VCH, Weinheim
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c) D. P. Curran, N. A. Porter, B. Giese, Stereochemistry of Radical Reactions, VCH, Weinheim, 1996;
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Stereochemistry of Radical Reactions
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Curran, D.P.1
Porter, N.A.2
Giese, B.3
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0004125345
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Masson, Paris
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Fossey, J.1
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0000893313
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Giese, B.1
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Trach, F.7
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