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Volumn 70, Issue 10, 2005, Pages 4073-4081

Formation of stable Meisenheimer adduct ion pairs in apolar solvents: Implications for stereoselective reactions

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIUM COMPOUNDS; AROMATIC COMPOUNDS; CHEMICAL REACTIONS; POSITIVE IONS; REACTION KINETICS; SALTS; SUBSTRATES;

EID: 18744398142     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0502495     Document Type: Article
Times cited : (16)

References (38)
  • 5
    • 0002630982 scopus 로고
    • For a comprehensive review on Meisenheimer adducts, see: Terrier, F. Chem. Rev. 1982, 82, 77-152.
    • (1982) Chem. Rev. , vol.82 , pp. 77-152
    • Terrier, F.1
  • 27
    • 18744364545 scopus 로고    scopus 로고
    • note
    • The EPR spectrum is provided in Supporting Information. It should be noted that radicals are often observed in solutions of aromatic compounds with bases and may not be associated with the formation of an adduct.
  • 28
    • 18744375570 scopus 로고    scopus 로고
    • note
    • Addition of concentrated HCl may potentially give rise to a nitronic acid, which could compromise some of the substrate.
  • 29
  • 32
    • 18744367347 scopus 로고    scopus 로고
    • note
    • 1H NMR) to those obtained after phase separation.
  • 33
    • 18744368864 scopus 로고    scopus 로고
    • note
    • As transfer of hydroxide ion between the aqueous layer and organic layer may be rate limiting, the extent of adduct formation could increase over time until equilibrium is achieved. In the case of substrate 1, however, there is no increase in adduct formation when reactions mixtures were allowed to stir for longer periods of time.
  • 36
    • 0028220741 scopus 로고
    • For a comprehensive review on the design of chiral selectors, see: Welch, C. J. Chromatogr. A, 1994, 666, 3-26.
    • (1994) J. Chromatogr. A , vol.666 , pp. 3-26
    • Welch, C.1
  • 38
    • 0004198952 scopus 로고
    • Wiley: New York
    • For a discussion of transition-state-theory, see: Klumpp, G. W. Reactivity in Organic Chemistry; Wiley: New York, 1982; pp 227-378.
    • (1982) Reactivity in Organic Chemistry , pp. 227-378
    • Klumpp, G.W.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.