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Volumn 44, Issue 29, 2005, Pages 4623-4626

Ambident reactivity of the nitrite ion revisited

Author keywords

HSAB principle; Kinetics; Klopman Salem equation; Kornblum's rule; Nitro compounds

Indexed keywords

ALKYLATION; CHEMICAL ACTIVATION; DIFFUSION; MIXTURES; REACTION KINETICS; THERMODYNAMICS;

EID: 22744453841     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200501274     Document Type: Article
Times cited : (54)

References (41)
  • 14
    • 0004272649 scopus 로고
    • Macmillan, New York
    • b) A. Streitwieser, C. H. Heathcock, E. M. Kosower, Introduction to Organic Chemistry, Macmillan, New York, 1992, p. 779; This statement is in line with Kornblum's report (p. 114 in ret. [1e]): "In the synthesis of saturated primary nitro compounds, silver nitrite gives nitro-paraffins in about 80% yield as against about 60% yields obtained with sodium nitrite. While silver nitrite is, therefore, the reagent of choice here, the lower cost and ready availability of sodium nitrite, the not very large disparity in yield, and the shorter reaction time all combine to make sodium nitrite an excellent second choice."
    • (1992) Introduction to Organic Chemistry , pp. 779
    • Streitwieser, A.1    Heathcock, C.H.2    Kosower, E.M.3
  • 17
  • 21
    • 22744449661 scopus 로고    scopus 로고
    • submitted
    • The laser flash photolysis was performed using state-of-the-art femtosecond pulses as excitation and light-emitting diodes (LEDs) as sources of monitoring beams. New instrumentation was developed that is compatible with standard pump probe setups. Details of this method will be published separately: U. Schmidhammer, S. Roth, E. Riedle, A. A. Tishkov, H. Mayr, Rev. Sci. Instrum. 2005, submitted.
    • (2005) Rev. Sci. Instrum.
    • Schmidhammer, U.1    Roth, S.2    Riedle, E.3    Tishkov, A.A.4    Mayr, H.5
  • 28
    • 22744458494 scopus 로고    scopus 로고
    • note
    • Because of the ease of the transformation of diarylnitromethanes into the corresponding benzophenones (see Scheme 2) these reactions were performed in NMR tubes and analyzed immediately after the reagents had been mixed.
  • 34
    • 0346047571 scopus 로고    scopus 로고
    • Neutral Thermochemical Data
    • (Eds.: P. J. Linstrom, W. G. Mallard), NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg MD, 20899
    • c) "Neutral Thermochemical Data": H. Y. Afeefy, J. F. Liebman, S. E. Stein in NIST Chemistry WebBook (Eds.: P. J. Linstrom, W. G. Mallard), NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg MD, 20899, 2003 (http://webbook.nist.gov).
    • (2003) NIST Chemistry WebBook
    • Afeefy, H.Y.1    Liebman, J.F.2    Stein, S.E.3
  • 36
    • 22744446789 scopus 로고    scopus 로고
    • note
    • 3N led to the immediate development of blue color characteristic for the corresponding benzhydryl cations.
  • 37
    • 1542680823 scopus 로고
    • 2 was reported to convert into benzophenone spontaneously: H. Feuer, H. Friedman, J. Org. Chem. 1975, 40, 187-190;
    • (1975) J. Org. Chem. , vol.40 , pp. 187-190
    • Feuer, H.1    Friedman, H.2
  • 40
    • 22744459408 scopus 로고    scopus 로고
    • see refs. [1a, c, f]
    • 2O (see refs. [1a, c, f]).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.