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28
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0005631255
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The iodoperfluoroalkylation of carbon-carbon unsaturated compounds such as alkenes and alkynes proceeds by a radical chain mechanism initiated by various radical initiators. However, the application of the photoinitiation to synthetic chemistry of organofluorous compounds has remained largely undeveloped, most probably due to the prejudice that the photoinitiation is an inefficient process. The photoinitiation, see for example: M.H. Habibi, and T.E. Mallouk J. Fluorine Chem. 53 1991 53
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24944432438
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43
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4644349439
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T. Fukuyama, Y. Uenoyama, S. Oguri, N. Otsuka, and I. Ryu Chem. Lett. 33 2004 854
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8244223866
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A. Ogawa, H. Yokoyama, T. Masawaki, K. Yokoyama, and N. Sonoda Phosphorus, Sulfur, Silicon 67 1992 219
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Ogawa, A.1
Yokoyama, H.2
Masawaki, T.3
Yokoyama, K.4
Sonoda, N.5
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47
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0001593661
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A. Ogawa, H. Yokoyama, K. Yokoyama, T. Masawaki, N. Kambe, and N. Sonoda J. Org. Chem. 56 1991 5721
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48
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A. Ogawa, N. Takami, M. Sekiguchi, H. Yokoyama, H. Kuniyasu, I. Ryu, and N. Sonoda Chem. Lett. 1991 2241
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49
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85113720008
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50
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0000346701
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For selenosulfonation of various unsaturated compounds, see for example: T.G. Back, and S. Collins J. Org. Chem. 46 1981 3249
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33845561611
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3B or metal as catalysts, see: N.O. Brace J. Org. Chem. 44 1979 212
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Brace, N.O.1
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0002265339
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P. Knochel Springer Berlin
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Maul, J.J.1
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Curran, D.P.5
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61
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24944491869
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note
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21IO: C, 25.83; H, 1.35. Found: C, 26.30; H, 1.58.
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62
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24944479245
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note
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21.
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63
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24944592595
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note
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9I).
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64
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24944500620
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note
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The cis/trans ratio corresponds to both the methylene groups bonded to the iodine and perfluoroalkyl groups. For the stereochemistry of the hydroxy group, both α- and β-isomers were formed in the ratio of ca. 1:1.
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65
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24944579300
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note
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21I, acyclic 1,2,6,7-adducts were not obtained at all, and acyclic 1,2-adducts were formed in 15% and 13% yield, respectively.
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66
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24944517802
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note
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For 7a, the stereochemistry of the major isomer is (1E,6E). As to the two minor products, the stereochemistry was tentatively assigned based on the comparison of the signals: (1E,6E)/(1E,6Z)/(1Z,6E) = 80/12/8. For 7b, similarly, (1E,6E)/(1E,6Z) = 91/9..
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67
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24944568649
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note
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The iodoperfluoroalkylation of 1-octyne and 1-octene proceeds with similar rates. Owing to the higher stability of vinylic iodides compared with alkyl iodides, however, the iodoperfluoroalkylation of alkynes sometimes takes place somewhat smoothly, compared with that of alkenes. See Refs. 4b and 12g.
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68
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24944577652
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note
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1H NMR. In the initial stage, the ratio of 9d / 10d was 66:34, and was changed to 72:28 upon irradiation for 1 h.
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