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Volumn 692, Issue 18, 2007, Pages 3892-3900

A new and highly effective organometallic approach to 1,2-dehalogenations and related reactions

Author keywords

Elimination; Reduction; Sodium; vic Diorganometals

Indexed keywords

DEHALOGENATION; FUNCTIONAL GROUPS; PROBES; REACTION KINETICS; REDUCTION; STEREOCHEMISTRY;

EID: 34548668242     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2007.05.039     Document Type: Article
Times cited : (11)

References (64)
  • 1
    • 0003543593 scopus 로고
    • For a list of reagents employed in reductive dehalogenation, see:, VCH Publishers, New York pp. 133-135
    • For a list of reagents employed in reductive dehalogenation, see:. Larock R.C. Comprehensive Organic Transformation (1989), VCH Publishers, New York pp. 133-135
    • (1989) Comprehensive Organic Transformation
    • Larock, R.C.1
  • 3
    • 11844304180 scopus 로고    scopus 로고
    • For a selection of relevant literature, see:
    • For a selection of relevant literature, see:. Concellón J.M., and Rodri{dotless}́guez-Solla H. Chem. Soc. Rev. 33 (2004) 599-609
    • (2004) Chem. Soc. Rev. , vol.33 , pp. 599-609
    • Concellón, J.M.1    Rodríguez-Solla, H.2
  • 15
    • 0004045862 scopus 로고
    • See, for example:, Reinhold Publishing Corporation, New York pp. 163-165
    • See, for example:. Fieser L.F., and Fieser M. Advanced Organic Chemistry (1961), Reinhold Publishing Corporation, New York pp. 163-165
    • (1961) Advanced Organic Chemistry
    • Fieser, L.F.1    Fieser, M.2
  • 16
    • 33947486579 scopus 로고
    • [2+2] cycloadditions:
    • [2+2] cycloadditions:. House H.O., and Cronin T.H. J. Org. Chem. 30 (1965) 1061-1070
    • (1965) J. Org. Chem. , vol.30 , pp. 1061-1070
    • House, H.O.1    Cronin, T.H.2
  • 18
    • 0000969134 scopus 로고
    • For a review on synthetic equivalents of acetylene in cycloaddition reactions, see:
    • For a review on synthetic equivalents of acetylene in cycloaddition reactions, see:. Lucchi D.O., and Modena G. Tetrahedron 40 (1984) 2585-2632
    • (1984) Tetrahedron , vol.40 , pp. 2585-2632
    • Lucchi, D.O.1    Modena, G.2
  • 25
    • 0041098023 scopus 로고
    • Ethene is a reasonable co-product of this reaction, but its formation was never ascertained
    • Ethene is a reasonable co-product of this reaction, but its formation was never ascertained. Reesor J.W.B., Smith J.G., and Wright G.F. J. Org. Chem. 19 (1954) 940-956
    • (1954) J. Org. Chem. , vol.19 , pp. 940-956
    • Reesor, J.W.B.1    Smith, J.G.2    Wright, G.F.3
  • 31
    • 34548676519 scopus 로고    scopus 로고
    • note
    • 2O or THF), weighed, and recycled to a successive reaction.
  • 32
    • 34548660967 scopus 로고    scopus 로고
    • note
    • Accordingly, trans-stilbazole can be recovered and purified by flash-chromatography (AcOEt/Petroleum Ether = 4:6) in 60-65% yield.
  • 33
    • 0000705453 scopus 로고
    • 2-Allyloxyphenol, 3e, is a pyrocathecol monoprotected with a group known to be unstable under reductive electron transfer reaction conditions.
    • 2-Allyloxyphenol, 3e, is a pyrocathecol monoprotected with a group known to be unstable under reductive electron transfer reaction conditions. Eisch J.J., and Jacobs A.M. J. Org. Chem. 28 (1963) 2145-2146
    • (1963) J. Org. Chem. , vol.28 , pp. 2145-2146
    • Eisch, J.J.1    Jacobs, A.M.2
  • 35
    • 0010495830 scopus 로고    scopus 로고
    • and references therein
    • Makosza M., and Grela K. Synlett (1997) 267-268 and references therein
    • (1997) Synlett , pp. 267-268
    • Makosza, M.1    Grela, K.2
  • 37
    • 0008440892 scopus 로고
    • and references therein
    • Pearson A.J., and Lee K. J. Org. Chem. 59 (1994) 2257-2260 and references therein
    • (1994) J. Org. Chem. , vol.59 , pp. 2257-2260
    • Pearson, A.J.1    Lee, K.2
  • 38
    • 34548667377 scopus 로고    scopus 로고
    • note
    • See Ref. [1b] for a comparison between these mechanisms. See Ref. [1i] for an in-depth discussion on competitive "inner-" and "outer-sphere" redox processes.
  • 40
    • 34548669067 scopus 로고    scopus 로고
    • note
    • α-Bromine-substituted radical intermediates are considered to be configurationally stabilized by bromine bridging. See Ref. [9a].
  • 43
    • 0026504140 scopus 로고
    • Na naphthalenide in 1,2-dimethoxyethane and references therein
    • Na naphthalenide in 1,2-dimethoxyethane. Pfaendler H.R., and Müller F.X. Synthesis (1992) 350-352 and references therein
    • (1992) Synthesis , pp. 350-352
    • Pfaendler, H.R.1    Müller, F.X.2
  • 46
    • 0041056928 scopus 로고
    • Literature references to starting materials: 2b:
    • Literature references to starting materials: 2b:. Fahey R.C., and Schneider H.-J. J. Am. Chem. Soc. 90 (1968) 4429-4434
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 4429-4434
    • Fahey, R.C.1    Schneider, H.-J.2
  • 48
    • 34548672068 scopus 로고    scopus 로고
    • 2d: see Ref. [24].
  • 51
    • 30544445581 scopus 로고
    • threo- and erythro-2h: Chem. Zentralbl. 106 (1935) 2358; Chem. Abstr. 29 (1935) 1062
    • threo- and erythro-2h:. Maruyama T. Proc. Imp. Acad. 10 (1934) 467-469 Chem. Zentralbl. 106 (1935) 2358; Chem. Abstr. 29 (1935) 1062
    • (1934) Proc. Imp. Acad. , vol.10 , pp. 467-469
    • Maruyama, T.1
  • 57
  • 59
    • 30544449328 scopus 로고
    • (E)-3g:
    • (E)-3g:. Rankoff G. Chem. Ber. 63 (1930) 2139-2142
    • (1930) Chem. Ber. , vol.63 , pp. 2139-2142
    • Rankoff, G.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.