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Volumn 65, Issue 20, 2000, Pages 6458-6461

A simple method for the synthesis of substituted benzylic ketones: Homologation of aldehydes via the in situ generation of aryldiazomethanes from aromatic aldehydes

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALDEHYDE; ALDEHYDE DERIVATIVE; ARYLDIAZOMETHANE; BENZYLIC KETONE; DIAZOMETHANE; HYDRAZONE DERIVATIVE; KETONE DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG;

EID: 0034613366     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000446y     Document Type: Article
Times cited : (46)

References (32)
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    • For leading references and reviews see: (a) Gutsche, C. D. Org. React. 1954, 8, 364-429. (b) Wulfman, D. S.; Linstrumelle, G.; Cooper, C. F. In The Chemistry of Diazonium and Diazo Groups; Patai, S., Ed.; Interscience: New York, 1978; p 821. (c) Maruoka, K.; Concepcion, A. B.; Yamamoto, H. J. Org. Chem. 1994, 59, 4725-4726. (e) Maruoka, K.; Concepcion, A. B.; Yamamoto, H. Synthesis 1994, 1283-1290.
    • (1954) Org. React. , vol.8 , pp. 364-429
    • Gutsche, C.D.1
  • 3
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    • Patai, S., Ed.; Interscience: New York
    • For leading references and reviews see: (a) Gutsche, C. D. Org. React. 1954, 8, 364-429. (b) Wulfman, D. S.; Linstrumelle, G.; Cooper, C. F. In The Chemistry of Diazonium and Diazo Groups; Patai, S., Ed.; Interscience: New York, 1978; p 821. (c) Maruoka, K.; Concepcion, A. B.; Yamamoto, H. J. Org. Chem. 1994, 59, 4725-4726. (e) Maruoka, K.; Concepcion, A. B.; Yamamoto, H. Synthesis 1994, 1283-1290.
    • (1978) The Chemistry of Diazonium and Diazo Groups , pp. 821
    • Wulfman, D.S.1    Linstrumelle, G.2    Cooper, C.F.3
  • 4
    • 0000716147 scopus 로고
    • For leading references and reviews see: (a) Gutsche, C. D. Org. React. 1954, 8, 364-429. (b) Wulfman, D. S.; Linstrumelle, G.; Cooper, C. F. In The Chemistry of Diazonium and Diazo Groups; Patai, S., Ed.; Interscience: New York, 1978; p 821. (c) Maruoka, K.; Concepcion, A. B.; Yamamoto, H. J. Org. Chem. 1994, 59, 4725-4726. (e) Maruoka, K.; Concepcion, A. B.; Yamamoto, H. Synthesis 1994, 1283-1290.
    • (1994) J. Org. Chem. , vol.59 , pp. 4725-4726
    • Maruoka, K.1    Concepcion, A.B.2    Yamamoto, H.3
  • 5
    • 0028643547 scopus 로고
    • For leading references and reviews see: (a) Gutsche, C. D. Org. React. 1954, 8, 364-429. (b) Wulfman, D. S.; Linstrumelle, G.; Cooper, C. F. In The Chemistry of Diazonium and Diazo Groups; Patai, S., Ed.; Interscience: New York, 1978; p 821. (c) Maruoka, K.; Concepcion, A. B.; Yamamoto, H. J. Org. Chem. 1994, 59, 4725-4726. (e) Maruoka, K.; Concepcion, A. B.; Yamamoto, H. Synthesis 1994, 1283-1290.
    • (1994) Synthesis , pp. 1283-1290
    • Maruoka, K.1    Concepcion, A.B.2    Yamamoto, H.3
  • 13
    • 0001645502 scopus 로고
    • For methods to prepare aryldiazomethanes see: (a) Creary, X. J. Am. Chem. Soc. 1980, 102, 1611-1618. (b) Creary, X. Org. Synth. 1985, 64, 207-216. (c) Overberger, C. G.; Anselme, J.-P. J. Org. Chem. 1963, 28, 592-593. (d) Kaufman, G. M.; Smith, J. A.; VanderStouw, G. G.; Shechter, H. J. Am. Chem. Soc. 1965, 87, 935-937.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 1611-1618
    • Creary, X.1
  • 14
    • 0001645502 scopus 로고
    • For methods to prepare aryldiazomethanes see: (a) Creary, X. J. Am. Chem. Soc. 1980, 102, 1611-1618. (b) Creary, X. Org. Synth. 1985, 64, 207-216. (c) Overberger, C. G.; Anselme, J.-P. J. Org. Chem. 1963, 28, 592-593. (d) Kaufman, G. M.; Smith, J. A.; VanderStouw, G. G.; Shechter, H. J. Am. Chem. Soc. 1965, 87, 935-937.
    • (1985) Org. Synth. , vol.64 , pp. 207-216
    • Creary, X.1
  • 15
    • 0000907776 scopus 로고
    • For methods to prepare aryldiazomethanes see: (a) Creary, X. J. Am. Chem. Soc. 1980, 102, 1611-1618. (b) Creary, X. Org. Synth. 1985, 64, 207-216. (c) Overberger, C. G.; Anselme, J.-P. J. Org. Chem. 1963, 28, 592-593. (d) Kaufman, G. M.; Smith, J. A.; VanderStouw, G. G.; Shechter, H. J. Am. Chem. Soc. 1965, 87, 935-937.
    • (1963) J. Org. Chem. , vol.28 , pp. 592-593
    • Overberger, C.G.1    Anselme, J.-P.2
  • 16
    • 0001313088 scopus 로고
    • For methods to prepare aryldiazomethanes see: (a) Creary, X. J. Am. Chem. Soc. 1980, 102, 1611-1618. (b) Creary, X. Org. Synth. 1985, 64, 207-216. (c) Overberger, C. G.; Anselme, J.-P. J. Org. Chem. 1963, 28, 592-593. (d) Kaufman, G. M.; Smith, J. A.; VanderStouw, G. G.; Shechter, H. J. Am. Chem. Soc. 1965, 87, 935-937.
    • (1965) J. Am. Chem. Soc. , vol.87 , pp. 935-937
    • Kaufman, G.M.1    Smith, J.A.2    VanderStouw, G.G.3    Shechter, H.4
  • 17
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    • Bamford, W. R.; Stevens, T. S. J. Chem. Soc. 1952, 4735-4740. This reference contains a study following the conversion of benzaldehyde tosylhydrazone to phenyldiazomethane in ethanol and monitors its concentration at periodic intervals over 24 h.
    • (1952) J. Chem. Soc. , pp. 4735-4740
    • Bamford, W.R.1    Stevens, T.S.2
  • 22
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    • For discussions of the stability of diazo compounds to protic solvents: (a) Finneman, J. I.; Fishbein, J. C. J. Org. Chem. 1994, 59, 6251-6256. (b) Finneman, J. I.; Fishbein, J. C. J. Am. Chem. Soc. 1995, 117, 4228-4239. See also ref 6.
    • (1994) J. Org. Chem. , vol.59 , pp. 6251-6256
    • Finneman, J.I.1    Fishbein, J.C.2
  • 23
    • 0001255481 scopus 로고
    • For discussions of the stability of diazo compounds to protic solvents: (a) Finneman, J. I.; Fishbein, J. C. J. Org. Chem. 1994, 59, 6251-6256. (b) Finneman, J. I.; Fishbein, J. C. J. Am. Chem. Soc. 1995, 117, 4228-4239. See also ref 6.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 4228-4239
    • Finneman, J.I.1    Fishbein, J.C.2
  • 30
    • 0343664268 scopus 로고    scopus 로고
    • Compound 17a, deoxybenzoin, is commercially available from Aldrich
    • Compound 17a, deoxybenzoin, is commercially available from Aldrich.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.