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Ogawa A., Tanaka H., Yokoyama H., Obayashi R., Yokoyama K., Sonoda N. J. Org. Chem. 57:1992;111.
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Ogawa A., Ogawa I., Obayashi R., Umezu K., Doi M., Hirao T. J. Org. Chem. 64:1999;86.
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Ogawa A., Doi M., Ogawa I., Hirao T. Angew. Chem., Int. Ed. 38:1999;2027.
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Tsuchii K., Doi M., Hirao T., Ogawa A. Angew. Chem., Int. Ed. 42:2003;3490.
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14
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0030666280
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For the introduction of both fluoroalkyl and phenylseleno groups into olefins by electroreduction, see: (a) Uneyama, K.; Yanagiguchi, T.; Asai, H. Tetrahedron Lett. 1997, 38, 7763; (b) Asai, H.; Uneyama, K. Chem. Lett. 1995, 1123; (c) Uneyama, K.; Kanai, M. Tetrahedron Lett. 1991, 32, 7425; (d) Uneyama, K.; Kitagawa, K. Tetrahedron Lett. 1991, 32, 3385.
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Uneyama, K.1
Yanagiguchi, T.2
Asai, H.3
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15
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0030666280
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For the introduction of both fluoroalkyl and phenylseleno groups into olefins by electroreduction, see: (a) Uneyama, K.; Yanagiguchi, T.; Asai, H. Tetrahedron Lett. 1997, 38, 7763; (b) Asai, H.; Uneyama, K. Chem. Lett. 1995, 1123; (c) Uneyama, K.; Kanai, M. Tetrahedron Lett. 1991, 32, 7425; (d) Uneyama, K.; Kitagawa, K. Tetrahedron Lett. 1991, 32, 3385.
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(1995)
Chem. Lett.
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Asai, H.1
Uneyama, K.2
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16
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0026334184
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For the introduction of both fluoroalkyl and phenylseleno groups into olefins by electroreduction, see: (a) Uneyama, K.; Yanagiguchi, T.; Asai, H. Tetrahedron Lett. 1997, 38, 7763; (b) Asai, H.; Uneyama, K. Chem. Lett. 1995, 1123; (c) Uneyama, K.; Kanai, M. Tetrahedron Lett. 1991, 32, 7425; (d) Uneyama, K.; Kitagawa, K. Tetrahedron Lett. 1991, 32, 3385.
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(1991)
Tetrahedron Lett.
, vol.32
, pp. 7425
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Uneyama, K.1
Kanai, M.2
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17
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0025853067
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For the introduction of both fluoroalkyl and phenylseleno groups into olefins by electroreduction, see: (a) Uneyama, K.; Yanagiguchi, T.; Asai, H. Tetrahedron Lett. 1997, 38, 7763; (b) Asai, H.; Uneyama, K. Chem. Lett. 1995, 1123; (c) Uneyama, K.; Kanai, M. Tetrahedron Lett. 1991, 32, 7425; (d) Uneyama, K.; Kitagawa, K. Tetrahedron Lett. 1991, 32, 3385.
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(1991)
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, pp. 3385
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Uneyama, K.1
Kitagawa, K.2
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26
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0035952978
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f-I, giving the corresponding β-iodoallylic perfluoroalkanes regioselectively in good yields, see: Ogawa, A.; Imura, M.; Kamada, N.; Hirao, T. Tetrahedron Lett. 2001, 42, 2489.
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(2001)
Tetrahedron Lett.
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Ogawa, A.1
Imura, M.2
Kamada, N.3
Hirao, T.4
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32
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85030950064
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f-I, and acetylenes in BTF homogeneous
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f-I, and acetylenes in BTF homogeneous.
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33
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85030939196
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This selenoperfluoroalkylation can proceed in shorter reaction time: irradiation for 1.5 h resulted in the formation of 7a in 53% yield.
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This selenoperfluoroalkylation can proceed in shorter reaction time: irradiation for 1.5 h resulted in the formation of 7a in 53% yield.
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34
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85030947062
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2 adduct to acetylenes (8) was formed as a byproduct
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2 adduct to acetylenes (8) was formed as a byproduct.
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35
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85030947459
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Noteworthy is the excellent stereoselectivity of this selenoperfluoroalkylation. The bisselenation of acetylenes also proceeds, with high stereoselectivity in the initial stage, and however, E to Z isomerization takes place gradually and finally the reaction provides a stereoisomeric mixture based on the thermodynamical stability of both isomers
-
Noteworthy is the excellent stereoselectivity of this selenoperfluoroalkylation. The bisselenation of acetylenes also proceeds, with high stereoselectivity in the initial stage, and however, E to Z isomerization takes place gradually and finally the reaction provides a stereoisomeric mixture based on the thermodynamical stability of both isomers.
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36
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85030936470
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21Se: 777.9690, found: 777.9686
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21Se: 777.9690, found: 777.9686.
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37
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85030937731
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It is also possible to purify the products by preparative TLC (or column chromatography) on silica gel (n-hexane)
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It is also possible to purify the products by preparative TLC (or column chromatography) on silica gel (n-hexane).
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38
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0346524343
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In general, vinylic radicals are believed to be a stereoisomeric mixture of σ-radicals, and a fast equilibrium is present between the stereoisomers, see:
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In general, vinylic radicals are believed to be a stereoisomeric mixture of σ-radicals, and a fast equilibrium is present between the stereoisomers, see: Fessenden R.W., Schuler R.H. J. Chem. Phys. 39:1963;2147.
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J. Chem. Phys.
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Fessenden, R.W.1
Schuler, R.H.2
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40
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0001304578
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The selenoperfluoroalkylation of ethyl propiolate requires long period of reaction time. Ethyl propiolate is assumed to generate vinylic π-radical, see: (a) Galli, C.; Guarnieri, A.; Koch, H.; Mencarelli, P.; Rappoport, Z. J. Org. Chem. 1997, 62, 4072; (b) Rubin, H.; Fischer, H. Helv. Chim. Acta 1996, 79, 1670; (c) Metzger, J. O.; Blumenstein, M. Chem. Ber. 1993, 126, 2493.
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Galli, C.1
Guarnieri, A.2
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Mencarelli, P.4
Rappoport, Z.5
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41
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0141440683
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The selenoperfluoroalkylation of ethyl propiolate requires long period of reaction time. Ethyl propiolate is assumed to generate vinylic π-radical, see: (a) Galli, C.; Guarnieri, A.; Koch, H.; Mencarelli, P.; Rappoport, Z. J. Org. Chem. 1997, 62, 4072; (b) Rubin, H.; Fischer, H. Helv. Chim. Acta 1996, 79, 1670; (c) Metzger, J. O.; Blumenstein, M. Chem. Ber. 1993, 126, 2493.
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(1996)
Helv. Chim. Acta
, vol.79
, pp. 1670
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Rubin, H.1
Fischer, H.2
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42
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0001403623
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The selenoperfluoroalkylation of ethyl propiolate requires long period of reaction time. Ethyl propiolate is assumed to generate vinylic π-radical, see: (a) Galli, C.; Guarnieri, A.; Koch, H.; Mencarelli, P.; Rappoport, Z. J. Org. Chem. 1997, 62, 4072; (b) Rubin, H.; Fischer, H. Helv. Chim. Acta 1996, 79, 1670; (c) Metzger, J. O.; Blumenstein, M. Chem. Ber. 1993, 126, 2493.
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(1993)
Chem. Ber.
, vol.126
, pp. 2493
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Metzger, J.O.1
Blumenstein, M.2
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43
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85030942599
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2 was conducted, most of the starting trimethylsilylacetylene was also recovered
-
2 was conducted, most of the starting trimethylsilylacetylene was also recovered.
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