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Volumn 46, Issue 42, 2005, Pages 7275-7278

A facile photoinduced iodoperfluoroalkylation of dienes, diynes, and enynes with perfluoroalkyl iodides via selective radical cyclization

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALKYL GROUP;

EID: 24944591745     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.07.088     Document Type: Article
Times cited : (25)

References (68)
  • 28
    • 0005631255 scopus 로고
    • 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
    • (1991) J. Fluorine Chem. , vol.53 , pp. 53
    • Habibi, M.H.1    Mallouk, T.E.2
  • 33
    • 24944432438 scopus 로고    scopus 로고
    • note
    • 11.
  • 50
    • 0000346701 scopus 로고
    • For selenosulfonation of various unsaturated compounds, see for example: T.G. Back, and S. Collins J. Org. Chem. 46 1981 3249
    • (1981) J. Org. Chem. , vol.46 , pp. 3249
    • Back, T.G.1    Collins, S.2
  • 54
    • 33845561611 scopus 로고
    • 3B or metal as catalysts, see: N.O. Brace J. Org. Chem. 44 1979 212
    • (1979) J. Org. Chem. , vol.44 , pp. 212
    • Brace, N.O.1
  • 61
    • 24944491869 scopus 로고    scopus 로고
    • note
    • 21IO: C, 25.83; H, 1.35. Found: C, 26.30; H, 1.58.
  • 62
    • 24944479245 scopus 로고    scopus 로고
    • note
    • 21.
  • 63
    • 24944592595 scopus 로고    scopus 로고
    • note
    • 9I).
  • 64
    • 24944500620 scopus 로고    scopus 로고
    • note
    • 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.
  • 65
    • 24944579300 scopus 로고    scopus 로고
    • note
    • 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.
  • 66
    • 24944517802 scopus 로고    scopus 로고
    • note
    • 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..
  • 67
    • 24944568649 scopus 로고    scopus 로고
    • note
    • 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.
  • 68
    • 24944577652 scopus 로고    scopus 로고
    • note
    • 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.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.