메뉴 건너뛰기




Volumn 74, Issue 12, 2009, Pages 4619-4622

An expeditious entry to 9-azabicyclo[3.3.1]nonane N-oxyl (ABNO): Another highly active organocatalyst for oxidation of alcohols

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL COMPOUNDS; CHEMICAL EQUATIONS; NITROXYL RADICAL; ORGANOCATALYST; OXIDATION OF ALCOHOLS; SYNTHETIC ROUTES;

EID: 67249095068     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900486w     Document Type: Article
Times cited : (115)

References (51)
  • 2
    • 47349116008 scopus 로고    scopus 로고
    • For recent reviews, see
    • For recent reviews, see: (a) Vogler, T.; Studer, A. Synthesis 2008, 1979-1993.
    • (2008) Synthesis , pp. 1979-1993
    • Vogler, T.1    Studer, A.2
  • 28
    • 67249092724 scopus 로고    scopus 로고
    • note
    • Hindrance around a nitroxyl radical center was believed to be an essential requirement for a nitroxyl radical to be stable, because simple nitroxyl radicals with an α-hydrogen underwent rapid disproportionation to their corresponding nitrone and hydroxyl amine.
  • 29
    • 33847519130 scopus 로고
    • Dupeyre and Rassat reported the synthesis of norpseudopelletierine N-oxyl {9-azabicyclo[3.3.1]nonane-3-one N-oxyl} as the first stable unhindered nitroxyl radical, in which any nitrone formation would be prohibited by Bredt's rule. Since then, a panel of bridged-bicyclic unhindered nitroxyl radicals have been synthesized
    • Dupeyre and Rassat reported the synthesis of norpseudopelletierine N-oxyl {9-azabicyclo[3.3.1]nonane-3-one N-oxyl} as the first stable unhindered nitroxyl radical, in which any nitrone formation would be prohibited by Bredt's rule. Since then, a panel of bridged-bicyclic unhindered nitroxyl radicals have been synthesized. (a) Dupeyre, R. M.; Rassat, A. Tetrahedron Lett. 1975, 16, 1839-1840.
    • (1975) Tetrahedron Lett. , vol.16 , pp. 1839-1840
    • Dupeyre, R.M.1    Rassat, A.2
  • 33
    • 27944474342 scopus 로고    scopus 로고
    • Rychnovsky and Farmer et al. demonstrated for the first time that unhindered nitroxyl radicals indeed worked as catalysts in alcohol oxidations. However, since their research interest was focused on the development of enantioselective catalysts, the catalytic efficiency of the elaborated C2-symmetric derivative of ABNO was not further examined
    • Rychnovsky and Farmer et al. demonstrated for the first time that unhindered nitroxyl radicals indeed worked as catalysts in alcohol oxidations. However, since their research interest was focused on the development of enantioselective catalysts, the catalytic efficiency of the elaborated C2-symmetric derivative of ABNO was not further examined. Graetz, B.; Rychnovsky, S.; Leu, W.-H.; Farmer, P.; Lin, R. Tetrahedron: Asymmetry 2005, 16, 3584-3598.
    • (2005) Tetrahedron: Asymmetry , vol.16 , pp. 3584-3598
    • Graetz, B.1    Rychnovsky, S.2    Leu, W.-H.3    Farmer, P.4    Lin, R.5
  • 34
    • 36549021985 scopus 로고    scopus 로고
    • In 2008, Onomura et al. reported the synthesis of a panel of azabicyclo N-oxyls and preliminary results on the electrochemical oxidation of alcohols using them as mediators to confirm their potential for the electrochemical oxidation of hindered secondary alcohols. However, they offer few comments on the efficiency of azabicyclo nitroxyl radicals toward oxidation of various alcohols under chemical conditions
    • In 2008, Onomura et al. reported the synthesis of a panel of azabicyclo N-oxyls and preliminary results on the electrochemical oxidation of alcohols using them as mediators to confirm their potential for the electrochemical oxidation of hindered secondary alcohols. However, they offer few comments on the efficiency of azabicyclo nitroxyl radicals toward oxidation of various alcohols under chemical conditions. (a) Demizu, Y.; Shiigi, H.; Oda, T.; Matsumura, Y.; Onomura, O. Tetrahedron Lett. 2008, 49, 48-52.
    • (2008) Tetrahedron Lett. , vol.49 , pp. 48-52
    • Demizu, Y.1    Shiigi, H.2    Oda, T.3    Matsumura, Y.4    Onomura, O.5
  • 36
    • 67249116352 scopus 로고    scopus 로고
    • note
    • Ingold et al. reported that the decomposition rate of 9-azabiclo[3.3.1]nonane N-oxyl (ABNO) (3) was very slow, while 8-azabicylo[3.2.1]octane N-oxyl (4) dimerized irreversibly.11
  • 37
    • 67249135154 scopus 로고    scopus 로고
    • note
    • Rychnovsky et al. also reported that 2,5-dimethylbicyclo[2.2.1]heptane N-oxyl (5) was too unstable to isolate.
  • 38
    • 67249160967 scopus 로고    scopus 로고
    • note
    • We also synthesized 8-azabicyclo[3.2.1]octane and 7-azabicyclo[2.2.1] heptane and attemped their oxidation to the corresponding nitroxyl radicals. However, we failed to isolate these nitroxyl radicals; instead, the corresponding hydroxylamines were recovered.
  • 49
    • 0000495151 scopus 로고
    • Huang-Minlon
    • Huang-Minlon, J. Am. Chem. Soc. 1949, 71, 3301.
    • (1949) J. Am. Chem. Soc. , vol.71 , pp. 3301
  • 50
    • 67249145426 scopus 로고    scopus 로고
    • note
    • We speculate that the difference came from the stability of the oxoammonium ion generated in the catalytic cycle. For notes on the instability of 9-oxo-9-azabicyclo[3.3.1]nonane oxoammonium ion, see ref 20c.
  • 51
    • 67249103540 scopus 로고    scopus 로고
    • note
    • 8a


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.