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Volumn 65, Issue 16, 2000, Pages 5043-5047

Free-radical reaction of imine derivatives in water

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA AMINO ACID; FREE RADICAL; IMINE; WATER;

EID: 0034637622     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000318+     Document Type: Article
Times cited : (105)

References (45)
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    • Triethylborane can be applied to the radical reactions in water. For discussion of triethylborane-mediated radical reactions in aqueous media, see: (a) Yamazaki, O.; Togo, H.; Nogami, G.; Yokoyama, M. Bull. Chem. Soc. Jpn. 1997, 70, 2519.
    • (1997) Bull. Chem. Soc. Jpn. , vol.70 , pp. 2519
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    • Alkyl radical can be generated via sonication of alkyl iodide in the presence of Zn/CuI in water
    • (c) Nakamura, T.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Synlett 1998, 1351. Alkyl radical can be generated via sonication of alkyl iodide in the presence of Zn/CuI in water. See:
    • (1998) Synlett , pp. 1351
    • Nakamura, T.1    Yorimitsu, H.2    Shinokubo, H.3    Oshima, K.4
  • 24
    • 0002047232 scopus 로고    scopus 로고
    • Because the glyoxylic oxime ether is activated by an electron-withdrawing substituent, it has high reactivity toward nucleophilic carbon radicals. See: (a) Miyabe, H.; Ushiro, C.; Naito, T. Chem. Commun. 1997, 1789.
    • (1997) Chem. Commun. , pp. 1789
    • Miyabe, H.1    Ushiro, C.2    Naito, T.3
  • 28
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    • (e) Miyabe, H.; Ushiro, C.; Ueda, M.; Yamakawa, K.; Naito, T. J. Org. Chem. 2000, 65, 176. For the complete reaction and selective alkylation, the excesses of reagents were employed. For example, treatment of oxime ether 1 with isopropyl iodide (1 equiv) and a commercially available 1.0 M solution of triethylborane in hexane (1 equiv) in water gave the isopropylated adduct 2 (13%) accompanied by the ethylated adduct (13%) and the recovered oxime ether 1 (70%).
    • (2000) J. Org. Chem. , vol.65 , pp. 176
    • Miyabe, H.1    Ushiro, C.2    Ueda, M.3    Yamakawa, K.4    Naito, T.5
  • 32
    • 0343051163 scopus 로고    scopus 로고
    • Oxime ether 3 and oxime 4 showed high solubility in water; however, hydrazone 5 and nitrons 6 were insoluble in water
    • Oxime ether 3 and oxime 4 showed high solubility in water; however, hydrazone 5 and nitrons 6 were insoluble in water.
  • 35
    • 0030020575 scopus 로고    scopus 로고
    • Nitrones have evolved as a useful trap for short-lived reactive free radicals. See: Becker, D, A. D. J. Am. Chem. Soc. 1996, 118, 905.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 905
    • Becker, D.A.D.1
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    • The radical addition to formaldoxime ether 11 in organic solvents, see: (a) Hart, D. J.; Seely, F. L. J. Am. Chem. Soc. 1988, 110, 1631.
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    • Hart, D.J.1    Seely, F.L.2
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    • (b) Chem. Rev. 1997, 97, 347-510 (Special Issue).
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.