Oxidative aromatization of 9,10-dihydroanthracenes using molecular oxygen promoted by activated carbon

Journal of Organic Chemistry

Volumn 68, Issue 21, 2003, Pages 8272-8273

  Nakamichi, Natsuki ^a   Kawabata, Hirotoshi ^a   Hayashi, Masahiko ^a  

^a KOBE UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

OXIDANTS;

ACTIVATED CARBON; OXIDATION; SUBSTITUTION REACTIONS; XYLENE;

AROMATIZATION;

9,10 DIHYDROANTHRACENE DERIVATIVE; ACTIVATED CARBON; ANTHRACENE DERIVATIVE; OXYGEN DERIVATIVE; UNCLASSIFIED DRUG; XYLENE;

AROMATIZATION; ARTICLE; OXIDATION; OXIDATION KINETICS; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 0142026478     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034995q     Document Type: Article

References (17)

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12. We recently reported the Pd/C catalyzed oxidative aromatization of 1,3,5-trisubstituted pyrazolines and Hantzsch 1,4-dihydropyridines; Nakamichi, N.; Kawashita, Y.; Hayashi, M. Org. Lett. 2002, 4, 3955.
13. Only slow conversion was observed even in the absence of catalysts (120 °C, 15 h, 8% yield).
14. The contents of metals other than Fe in Darco KB which might concern this oxidative aromatization were as follows (ppm): Cu, 16.8 ppm; Mn, 9.99 ppm; Cr, 6.81 ppm. The contents of all metals in Darco KB, Darco KB-B, and Darco G-60 are listed in the Supporting Information.
15. The present activated carbon (Darco KB, Aldrich, Inc.) also promoted the reaction of Hantzsch 1,4-dihydropyridine to afford the corresponding pyridine derivative in high yield. The detail of this reaction will be published soon.
16. We used an inexpensive mixture of o-, m-, and p-xylene.
17. Merck Index, 13th ed.; Merck: Boca Raton, 2001; p 115.