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Volumn 127, Issue 16, 2005, Pages 5957-5963

The mechanism of selective purine C-nitration revealed: NMR studies demonstrate formation and radical rearrangement of an N7-nitramine intermediate

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIUM COMPOUNDS; ELECTRON TRAPS; NEGATIVE IONS; NITRATION; NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTIONS;

EID: 17744397327     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja042590x     Document Type: Article
Times cited : (19)

References (63)
  • 7
    • 0037467683 scopus 로고    scopus 로고
    • Several recent examples include: (a) Prekupec, S.; Svedrui, D.; Gazivoda, T.; Mrvo-Sermek, D.; Nagl, A.; Grdia, M.; Paveli, K.; Balzarini, J.; De Clercq, E.; Folkers, G.; Scapozza, L.; Mintas, M.; Rai-Mali, S. J. Med. Chem. 2003, 46, 5763-5772. (b) Hocek, M.; Votruba, I.; Dvorakova, H. Tetrahedron 2003, 59, 607-611.
    • (2003) Tetrahedron , vol.59 , pp. 607-611
    • Hocek, M.1    Votruba, I.2    Dvorakova, H.3
  • 9
    • 17744372657 scopus 로고    scopus 로고
    • Several recent examples include: (a) Diwan, P.; Lacasse, J. J.; Schang, L. M. J. Virol. 2004, 78, 4431-4434. (b) Chen, X.; Kern, E. R.; Drach, J. C.; Gullen, E.; Cheng, Y.-C.; Zemlicka, J. J. Med. Chem. 2003, 46, 1531-1537.
    • (2004) J. Virol. , vol.78 , pp. 4431-4434
    • Diwan, P.1    Lacasse, J.J.2    Schang, L.M.3
  • 11
    • 17744390326 scopus 로고    scopus 로고
    • note
    • Abbreviations used in the text: Boc (tert-butoxycarbonyl), DMAP (4-N,N-(dimethylamino)pyridine), TBAN (tetrabutylammonium nitrate), TFA (trifluoroacetic acid), TFAA (trifluoroacetic anhydride), TFAN (trifluoroacetyl nitrate), OTFA (trifluoroacetoxy).
  • 32
    • 17744388520 scopus 로고
    • Schofield, K., Ed.; Cambridge University Press: Cambridge, Chapter 15
    • Moodie, R. B. Aromatic Nitration; Schofield, K., Ed.; Cambridge University Press: Cambridge, 1980; Chapter 15.
    • (1980) Aromatic Nitration
    • Moodie, R.B.1
  • 37
    • 17744383135 scopus 로고    scopus 로고
    • note
    • The composition of the sample did not change when placed in a freezer at -80°C; after 5 months, still no conversion of the intermediate to the end product had occurred.
  • 44
    • 0000907108 scopus 로고
    • P was found by Ridd and co-workers during the acid-catalyzed nitramine rearrangement of 2,6-dichloro-N-nitroaniline and 2,6-dibromo-N-nitroaniline: Abu-Namous, A. M. A.; Ridd, J. H.; Sandall, J. P. B. Can. J. Chem. 1986, 64, 1124-1129.
    • (1986) Can. J. Chem. , vol.64 , pp. 1124-1129
    • Abu-Namous, A.M.A.1    Ridd, J.H.2    Sandall, J.P.B.3
  • 49
    • 0001439304 scopus 로고
    • and earlier papers in this series
    • (b) White, W. N.; White, H. S.; Fentiman, A. J. Org. Chem. 1976, 41, 3166-3170 and earlier papers in this series.
    • (1976) J. Org. Chem. , vol.41 , pp. 3166-3170
    • White, W.N.1    White, H.S.2    Fentiman, A.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.