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Volumn 72, Issue 26, 2007, Pages 10123-10129

Nitration versus nitrosation chemistry of menthofuran: Remarkable fragmentation and dimerization pathways and expeditious entry into dehydromenthofurolactone

Author keywords

[No Author keywords available]

Indexed keywords

DIMERIZATION; NITRATION; NITRIC ACID; OXIDATION; PH EFFECTS; REACTION KINETICS;

EID: 84961983727     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701992r     Document Type: Article
Times cited : (13)

References (35)
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    • Herbal Medicine. Expanded Commission E Monographs; American Botanical Council, 2000 (see: http://www.herbalgram.org/youngliving/ HerbalMedicine/default.asp?m=65).
    • Herbal Medicine. Expanded Commission E Monographs; American Botanical Council, 2000 (see: http://www.herbalgram.org/youngliving/ HerbalMedicine/default.asp?m=65).
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    • 1H NMR resonances, while their IR spectra were completely superimposable.
    • 1H NMR resonances, while their IR spectra were completely superimposable.
  • 13
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    • The trapping reaction between 1 and carbonyl compounds is of general applicability and may lead to a variety of bisfuranyl adducts. For example, bisfuranyl adducts were easily obtained when 1 was treated with vanillin (54% yield, anisaldehyde (43, and furfural (39, in the presence of catalytic amounts of various acidic catalysts (H2SO4, p-toluenesulfonic acid, acidic Dowex resin, The reaction gives better yields with electron-rich carbonyl compounds, whereas no product was formed with benzaldehyde and aromatic aldehydes bearing electron-withdrawing groups o- and p-nitrobenzaldehyde, p-chlorobenzaldehyde, suggesting that protonation of the aldehyde carbonyl group is the critical step. A more detailed account of this reaction is out of the scope of this paper and will be reported elsewhere
    • 4, p-toluenesulfonic acid, acidic Dowex resin). The reaction gives better yields with electron-rich carbonyl compounds, whereas no product was formed with benzaldehyde and aromatic aldehydes bearing electron-withdrawing groups (o- and p-nitrobenzaldehyde, p-chlorobenzaldehyde), suggesting that protonation of the aldehyde carbonyl group is the critical step. A more detailed account of this reaction is out of the scope of this paper and will be reported elsewhere.
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    • Frisch, M. J, Trucks, G. W, Schlegel, H. B, Scuseria, G. E, Robb, M. A, Cheeseman, J. R, Montgomery, J. A, Jr, Vreven, T, Kudin, K. N, Burant, J. C, Millam, J. M, Iyengar, S. S, Tomasi, J, Barone, V, Mennucci, B, Cossi, M, Scalmani, G, Rega, N, Petersson, G. A, Nakatsuji, H, Hada, M, Ehara, M, Toyota, K, Fukuda, R, Hasegawa, J, Ishida, M, Nakajima, T, Honda, Y, Kitao, O, Nakai, H, Klene, M, Li, X, Knox, J. E, Hratchian, H. P, Cross, J. B, Bakken, V, Adamo, C, Jaramillo, J, Gomperts, R, Stratmann, R. E, Yazyev, O, Austin, A. J, Cammi, R, Pomelli, C, Ochterski, J. W, Ayala, P. Y, Morokuma, K, Voth, G. A, Salvador, P, Dannenberg, J. J, Zakrzewski, V. G, Dapprich, S, Daniels, A. D, Strain, M. C, Farkas, O, Malick, D. K, Rabuck, A. D, Raghavachari, K, Foresman, J. B, Ortiz, J. V, Cui, Q, Baboul, A. G, Clifford, S, Cioslowski, J, Stefanov, B. B, Liu, G, Liashenko, A, Piskorz, P, Komaromi, I, Martin, R. L, Fox, D. J, Keit
    • Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2003.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.