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Volumn 130, Issue 4, 2008, Pages 1148-1149

Tandem carbon-carbon and carbon-chlorine bond formation by Cu(II) chloride-promoted [3,3] sigmatropic rearrangement of N-allylhydrazones

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; CARBENE; CARBON; CARBONYL DERIVATIVE; CHLORINE; COPPER CHLORIDE; HYDRAZINE; HYDRAZONE DERIVATIVE; HYDROGEN;

EID: 38649094579     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja7101967     Document Type: Article
Times cited : (26)

References (23)
  • 1
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    • For a review, see:, Trost, B. M, Fleming, I, Eds, Pergamon Press: Oxford
    • (a) For a review, see: Hutchins, R. O. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 8.
    • (1991) Comprehensive Organic Chemistry , vol.8
    • Hutchins, R.O.1
  • 2
    • 2342460927 scopus 로고    scopus 로고
    • For recent advances, see
    • (b) For recent advances, see: Furrow, M. E.; Myers, A. G. J. Am. Chem. Soc. 2004, 126, 5436-5445.
    • (2004) J. Am. Chem. Soc , vol.126 , pp. 5436-5445
    • Furrow, M.E.1    Myers, A.G.2
  • 3
    • 0000652045 scopus 로고
    • For examples, see: a
    • For examples, see: (a) Stork, G.; Benaim, J. J. Am. Chem. Soc. 1971, 93, 5938-5939.
    • (1971) J. Am. Chem. Soc , vol.93 , pp. 5938-5939
    • Stork, G.1    Benaim, J.2
  • 15
    • 0031012804 scopus 로고    scopus 로고
    • Treatment of unsubstituted hydrazones with Cu(II) halides has been previously shown to afford geminal dihalides, see: (a) Takeda, T.; Sasaki, R.; Yamauchi, S.; Fujiwara, T. Tetrahedron 1997, 53, 557-566 and reference 1b for further details.
    • Treatment of unsubstituted hydrazones with Cu(II) halides has been previously shown to afford geminal dihalides, see: (a) Takeda, T.; Sasaki, R.; Yamauchi, S.; Fujiwara, T. Tetrahedron 1997, 53, 557-566 and reference 1b for further details.
  • 16
    • 33748975897 scopus 로고    scopus 로고
    • Alternatively, monochlorination may be achieved under Swern-type conditions, see
    • Alternatively, monochlorination may be achieved under Swern-type conditions, see: Brewer, M. Tetrahedron Lett. 2006, 47, 7731-7733.
    • (2006) Tetrahedron Lett , vol.47 , pp. 7731-7733
    • Brewer, M.1
  • 17
    • 1542430399 scopus 로고
    • For two other examples of one-flask carbon-carbon and carbon-halogen bond-forming reactions, see: a
    • For two other examples of one-flask carbon-carbon and carbon-halogen bond-forming reactions, see: (a) Oriyama, T.; Iwanami, K.; Tsukamoto, K.; Ichimura, Y.; Koga, G. Bull. Chem. Soc. Jpn. 1991, 64, 1410-1412.
    • (1991) Bull. Chem. Soc. Jpn , vol.64 , pp. 1410-1412
    • Oriyama, T.1    Iwanami, K.2    Tsukamoto, K.3    Ichimura, Y.4    Koga, G.5
  • 19
    • 38649085172 scopus 로고    scopus 로고
    • 2-2-methylprop-2-en-1-ol alcohol (see Supporting Information for further details).
    • 2-2-methylprop-2-en-1-ol alcohol (see Supporting Information for further details).
  • 20
    • 38649093177 scopus 로고    scopus 로고
    • An analogous experiment conducted by Stevens and co-workers showed that rearrangement of a non-Boc protected hydrazone at 300°C proceeded with 9% scrambling of the deuterium label, see ref. 5
    • An analogous experiment conducted by Stevens and co-workers showed that rearrangement of a non-Boc protected hydrazone at 300°C proceeded with 9% scrambling of the deuterium label, see ref. 5.
  • 21
    • 33847087938 scopus 로고    scopus 로고
    • 2 is known to be a good single electron oxidant of enolates to promote oxidative coupling, see: Ito, Y.; Konoike, T.; Harada, T.; Saegusa, T. J. Am. Chem. Soc. 1977, 99, 1487-1493.
    • 2 is known to be a good single electron oxidant of enolates to promote oxidative coupling, see: Ito, Y.; Konoike, T.; Harada, T.; Saegusa, T. J. Am. Chem. Soc. 1977, 99, 1487-1493.
  • 22
    • 0001307421 scopus 로고
    • For reviews, see: a
    • For reviews, see: (a) Bauld, N. L. Tetrahedron 1989, 45, 5307-5363.
    • (1989) Tetrahedron , vol.45 , pp. 5307-5363
    • Bauld, N.L.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.