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Volumn 75, Issue 23, 2010, Pages 8078-8087

Synthetic approaches to bicyclic diazenium salts

Author keywords

[No Author keywords available]

Indexed keywords

ARYL SUBSTITUENTS; HYDRAZONES; LEWIS ACID; SYNTHETIC APPROACH; TERMINAL OLEFINS;

EID: 78650266319     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101706h     Document Type: Article
Times cited : (13)

References (40)
  • 18
    • 78650289579 scopus 로고    scopus 로고
    • For a summary of other oxidants that effect this conversion but find less use see ref 16
    • For a summary of other oxidants that effect this conversion but find less use see ref 16.
  • 27
    • 78650275568 scopus 로고    scopus 로고
    • 2′ mechanism
    • 2′ mechanism.
  • 30
    • 0141741604 scopus 로고    scopus 로고
    • The log of the ratio of products obtained was used for these plots because (assuming the reaction is irreversible under the reaction conditions) these values are directly related to the free energy difference between the regioisomeric transition states. This relationship is analogus to using log(er) for Hammett plots of results obtained for enantioselective reactions. For an example of the use of log(er) in Hammett plots see
    • The log of the ratio of products obtained was used for these plots because (assuming the reaction is irreversible under the reaction conditions) these values are directly related to the free energy difference between the regioisomeric transition states. This relationship is analogus to using log(er) for Hammett plots of results obtained for enantioselective reactions. For an example of the use of log(er) in Hammett plots see: Constantine, R. N.; Kim, N.; Bunt, R. C. Org. Lett. 2003, 5, 2279
    • (2003) Org. Lett. , vol.5 , pp. 2279
    • Constantine, R.N.1    Kim, N.2    Bunt, R.C.3
  • 38
    • 78650274185 scopus 로고    scopus 로고
    • The hydrazones could also be prepared by mixing the ketone, 4-chlorophenyl hydrazine hydrochloride, and sodium acetate in ethanol under an atmosphere of nitrgen. The mixture was stirred at room temperature or heated to reflux (for sterically encumbered ketones) and the progress of the reaction was monitored by TLC. Upon completion, the solvent was removed in vacuo to provide the hydrazone, which could be further purified by dissolving the residue in pentane and passing the mixture through a short plug of basic alumina
    • The hydrazones could also be prepared by mixing the ketone, 4-chlorophenyl hydrazine hydrochloride, and sodium acetate in ethanol under an atmosphere of nitrgen. The mixture was stirred at room temperature or heated to reflux (for sterically encumbered ketones) and the progress of the reaction was monitored by TLC. Upon completion, the solvent was removed in vacuo to provide the hydrazone, which could be further purified by dissolving the residue in pentane and passing the mixture through a short plug of basic alumina.
  • 40
    • 78650282374 scopus 로고    scopus 로고
    • The aryl-α-chloroazoalkane products were moderately stable, but decomposed on standing. Attempts to send the sample for exact mass determination failed to provide useful data
    • The aryl-α-chloroazoalkane products were moderately stable, but decomposed on standing. Attempts to send the sample for exact mass determination failed to provide useful data.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.