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Volumn 65, Issue 9, 2000, Pages 2748-2754

Characterization via ESR spectroscopy, of radical intermediates in the photooxidation of arylcarbinols by ceric ammonium nitrate

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; ALCOHOL; AMMONIUM NITRATE; CERIUM NITRATE; NAPHTHYL GROUP; PROPANOL; RADICAL;

EID: 0034607973     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991856t     Document Type: Article
Times cited : (24)

References (38)
  • 1
    • 0342745921 scopus 로고    scopus 로고
    • note
    • In partial fulfillment of the requirements for a Ph.D. degree in Chemical Sciences, University of Bologna.
  • 9
    • 0344788999 scopus 로고    scopus 로고
    • The allyloxyl radicals were obtained by photolysis of the corresponding nitrites, generated directly via an exchange reaction between the appropriate allylic alcohol and tert-butyl nitrite, which also acted as the spin trap: (a) Grossi, L.; Strazzari, S. J. Chem. Soc., Chem. Commun. 1997, 917. (b) Grossi, L.; Strazzari, S.; Gilbert, B. C.; Whitwood, A. C. J. Org. Chem. 1998, 63, 8366.
    • (1997) J. Chem. Soc., Chem. Commun. , pp. 917
    • Grossi, L.1    Strazzari, S.2
  • 10
    • 0032515115 scopus 로고    scopus 로고
    • The allyloxyl radicals were obtained by photolysis of the corresponding nitrites, generated directly via an exchange reaction between the appropriate allylic alcohol and tert-butyl nitrite, which also acted as the spin trap: (a) Grossi, L.; Strazzari, S. J. Chem. Soc., Chem. Commun. 1997, 917. (b) Grossi, L.; Strazzari, S.; Gilbert, B. C.; Whitwood, A. C. J. Org. Chem. 1998, 63, 8366.
    • (1998) J. Org. Chem. , vol.63 , pp. 8366
    • Grossi, L.1    Strazzari, S.2    Gilbert, B.C.3    Whitwood, A.C.4
  • 18
    • 33947299611 scopus 로고
    • The use of cerium(IV) as a qualitative colorimetric reagent for the detection of alcohols has been known for a long time and even quantitative methods for the analysis of alcohols based on the red color of the Ce(IV)-alcohol complexes have been developed: (a) Young, L. B.; Trahanovsky, W. S. J. Am. Chem. Soc. 1969, 91, 5060. (b) Trahanovsky, W. S.; Macaulay, D. B. J. Org. Chem. 1973, 38, 1497.
    • (1969) J. Am. Chem. Soc. , vol.91 , pp. 5060
    • Young, L.B.1    Trahanovsky, W.S.2
  • 19
    • 0342272081 scopus 로고
    • The use of cerium(IV) as a qualitative colorimetric reagent for the detection of alcohols has been known for a long time and even quantitative methods for the analysis of alcohols based on the red color of the Ce(IV)-alcohol complexes have been developed: (a) Young, L. B.; Trahanovsky, W. S. J. Am. Chem. Soc. 1969, 91, 5060. (b) Trahanovsky, W. S.; Macaulay, D. B. J. Org. Chem. 1973, 38, 1497.
    • (1973) J. Org. Chem. , vol.38 , pp. 1497
    • Trahanovsky, W.S.1    Macaulay, D.B.2
  • 26
    • 0342745917 scopus 로고    scopus 로고
    • note
    • In this scheme, radical-radical termination of two alkoxyl radicals and of an alkoxyl and a carbon centered radical, yielding respectively a peroxide and an ether, have not be included. These reaction can in fact be assumed to be relatively unimportant both for the very low steady-state concentration of the alkoxyl radical, which rapidly undergoes β-scission and H-abstraction, and for the low energies involved in the formed bonds. Also, reaction 2 can be considered to follow a pseudo-first-order kinetic equation, since acetonitrile, present as the solvent in large excess, can be assumed not to change its concentration significantly.
  • 27
    • 0343180563 scopus 로고    scopus 로고
    • note
    • 5 must be multiplied by two.
  • 34
    • 0342310988 scopus 로고    scopus 로고
    • note
    • The synthesis of this substrate was performed following a procedure suggested by Prof. R. Leardini.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.