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Volumn 74, Issue 21, 2009, Pages 8064-8070

Tuning the reducing properties of 1,2-diaryl-1,2-disodiumethanes

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC RINGS; CARBANIONIC CENTERS; CHEMICAL EQUATIONS; ELECTROCHEMICAL ANALYSIS; ELECTRON DONORS; REDUCTION BEHAVIOR;

EID: 70350738417     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901183x     Document Type: Article
Times cited : (18)

References (61)
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  • 13
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    • and references cited therein
    • (a) Fürstenr, A.; Seidel, G. Synthesis 1995, 63-68 and references cited therein.
    • (1995) Synthesis , pp. 63-68
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  • 14
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    • and references cited therein
    • (b) Makosza, M.; Grela, K. Synlett 1997, 267-268 and references cited therein.
    • (1997) Synlett , pp. 267-268
    • Makosza, M.1    Grela, K.2
  • 18
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    • note
    • Our procedure could not be applied to the generation of p-methoxysubstituted dianions 2, due to competitive demethoxyation reactions (see ref 2a).
  • 19
    • 0011618447 scopus 로고
    • The electrochemical behavior of 1b-d, under various conditions, was already reported. 1b: (a) 1c
    • The electrochemical behavior of 1b-d, under various conditions, was already reported. 1b: (a) Farnia, G.; Maran, F.; Sandonà, G. J. Chem. Soc., Faraday Trans. I, 1986, 82, 1885-1892. 1c:
    • (1986) J. Chem. Soc., Faraday Trans. I , vol.82 , pp. 1885-1892
    • Farnia, G.1    Maran, F.2    Sandonà, G.3
  • 22
    • 70350723137 scopus 로고    scopus 로고
    • note
    • 3 = -2.780 V vs. SCE). We assigned it to the formation of a pyridine-type radical anion. Indeed, pyridine itself is electrochemically reduced in DMF at -2.76 V vs. SCE; similarly, mono-, di-, and trimethylpyridines are reduced with E° ranging from -2.77 and -2.91 V vs. SCE:
  • 28
    • 0001312964 scopus 로고
    • Bard, A. J., Ed.; Marcel Dekker: New York
    • Peover, M. E. In Electronalytical Chemistry; Bard, A. J., Ed.; Marcel Dekker: New York, 1967; Vol.2, pp 1-51.
    • (1967) Electronalytical Chemistry , vol.2 , pp. 1-51
    • Peover, M.E.1
  • 29
    • 70350735290 scopus 로고    scopus 로고
    • note
    • 17c Disproportionation mechanisms, however, may provide the actual reaction path when very weak proton donors are present or added (such as alcohols or water): for example, see refs 11b and 4-7 and ref 10 cited therein.
  • 32
    • 0003939938 scopus 로고    scopus 로고
    • For example, see: 4th ed.; Lund, H., Hammerich, O., Eds.; Marcel Dekker, Inc.: New York
    • (c) For example, see: Heinze, J. In Organic Electrochemistry, 4th ed.; Lund, H., Hammerich, O., Eds.; Marcel Dekker, Inc.: New York, 2001; pp 293-332.
    • (2001) Organic Electrochemistry , pp. 293-332
    • Heinze, J.1
  • 33
    • 0041609163 scopus 로고
    • The reduction of benzophenone with 1,2-disodium-1,2-diphenylethane was already reported
    • The reduction of benzophenone with 1,2-disodium-1,2-diphenylethane was already reported: Brook, A. G.; Cohen, H. L.; Wright, G. F. J. Org. Chem. 1953, 18, 447-463.
    • (1953) J. Org. Chem. , vol.18 , pp. 447-463
    • Brook, A.G.1    Cohen, H.L.2    Wright, G.F.3
  • 36
    • 0027416797 scopus 로고
    • For the generation and reactivity of the corresponding dilithium derivative, see
    • (c) For the generation and reactivity of the corresponding dilithium derivative, see: Guijarro, D.; Mancheño, B.; Yus, M. Tetrahedron 1993, 49, 1327-1334.
    • (1993) Tetrahedron , vol.49 , pp. 1327-1334
    • Guijarro, D.1    Mancheño, B.2    Yus, M.3
  • 37
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    • note
    • A reaction run with 1 equiv of 2d led to the recovery of a reaction mixture containing, besides 50% unreacted 4, 34% of 6a as well as 16% of 1,2-dihydxoxy-1,2,3,4-tetraphenylethane.
  • 38
    • 70350707057 scopus 로고    scopus 로고
    • note
    • Reduction of ketoester 7 to ketoacid 8 was run with 1 equiv of dianion 2b under inverse addition reaction conditions (see the Supporting Information).
  • 39
    • 70350737286 scopus 로고    scopus 로고
    • note
    • Under similar conditions, low conversions (12 to 13 and 14 to a mixture of 15 and 16) were observed performing these reactions in the presence of Na metal.
  • 58
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    • Adamson, D. W. J. Chem. Soc., Suppl. Issue No. 1 1949, S144-155.
    • (1949) J. Chem. Soc. , Issue.SUPPL. ISSUE NO. 1
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.