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Volumn 10, Issue 19, 2008, Pages 4155-4158

Stereoselective bromination reactions using tridecylmethylphosphonium tribromide in a "stacked" reactor

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EID: 61349193086     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801327n     Document Type: Article
Times cited : (40)

References (53)
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    • 61349135837 scopus 로고    scopus 로고
    • De Meijere, A, Diederich, F, Eds, 2nd ed, Wiley-VCH: Weinheim
    • (a) De Meijere, A.; Diederich, F., Eds. Metal-catalyzed Cross-coupling Reactions, 2nd ed.; Wiley-VCH: Weinheim, 2004.
    • (2004) Metal-catalyzed Cross-coupling Reactions
  • 25
    • 49249086707 scopus 로고    scopus 로고
    • Ionic Liquids IIIB: Fundamental, Progress, Challenges and Opportunities
    • Rogers, R. D, Seddon, K. R, Eds, American Chemical Society: Washington, DC, Chap 21, pp
    • (f) Abdallah, D. J.; Wauters, H. C.; Kwait, D. C.; Khetrapal, C. L.; Nagana Gowda, G. A.; Robertson, A.; Weiss, R. G. Ionic Liquids IIIB: Fundamental, Progress, Challenges and Opportunities (ACS Symposium Series 902); Rogers, R. D., Seddon, K. R., Eds.; American Chemical Society: Washington, DC, 2005; Chap 21, pp 303-320.
    • (2005) ACS Symposium Series , vol.902 , pp. 303-320
    • Abdallah, D.J.1    Wauters, H.C.2    Kwait, D.C.3    Khetrapal, C.L.4    Nagana Gowda, G.A.5    Robertson, A.6    Weiss, R.G.7
  • 36
    • 60849129709 scopus 로고
    • (a) Org. Synth. Coll.; 1941; Vol. 1, p 521.
    • (1941) Org. Synth. Coll , vol.1 , pp. 521
  • 37
    • 0346177003 scopus 로고
    • (b) Org. Synth. Coll.; 1943; Vol. 2, p 171.
    • (1943) Org. Synth. Coll , vol.2 , pp. 171
  • 41
    • 61349092466 scopus 로고    scopus 로고
    • We have not observed large differences in the outcomes of reactions conducted with the two salts. The synlanti ratio for products from cis-stilbene was 97/3 when 1P10Br was the initial salt in contact with the hexadecane layer as compared to 94/6 reported in Table 1 using 1P10Br3, However, use of 1P10Br3 is recommended in general because, in some cases, bromine that diffuses from below may react more slowly with the solid 1P10Br than it diffuses through the phosphonium layer and reacts with molecules in the upper hexadecane layer
    • 3 is recommended in general because, in some cases, bromine that diffuses from below may react more slowly with the solid 1P10Br than it diffuses through the phosphonium layer and reacts with molecules in the upper hexadecane layer.
  • 45
    • 33947468524 scopus 로고    scopus 로고
    • 2 freezes at -7.3 °C. J. Am. Chem. Soc. 1912, 34, 1273-1290.
    • 2 freezes at -7.3 °C. J. Am. Chem. Soc. 1912, 34, 1273-1290.
  • 46
    • 61349122232 scopus 로고    scopus 로고
    • We have not compared as yet the regio- and stereoselectivities of brominations using 1P10Br3 and 1P10Br5. The configurations of our systems strongly suggest that 1P10Br3 is the dominant brominating agent in the work reported here
    • 3 is the dominant brominating agent in the work reported here.
  • 47
    • 61349156927 scopus 로고    scopus 로고
    • A slightly more sophisticated apparatus, which allows for the direct addition of bromine to the bottom layer and direct removal of the hexadecane layers, has been designed, and results from experiments in which it is used will be reported in the future
    • A slightly more sophisticated apparatus, which allows for the direct addition of bromine to the bottom layer and direct removal of the hexadecane layers, has been designed, and results from experiments in which it is used will be reported in the future.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.