메뉴 건너뛰기




Volumn , Issue 26, 2007, Pages 4431-4436

In situ generation of nitroso compounds from catalytic hydrogen peroxide oxidation of primary aromatic amines and their one-pot use in hetero-Diels-Alder reactions

Author keywords

Aniline oxidation; Aqueous hydrogen peroxide; Nitroso compounds; Selenium; Tandem reaction

Indexed keywords


EID: 34548731325     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700368     Document Type: Article
Times cited : (58)

References (69)
  • 9
    • 0142169492 scopus 로고    scopus 로고
    • For recent reviews on nitroso ene reactions, see
    • For recent reviews on nitroso ene reactions, see: W. Adam, O. Krebs, Chem. Rev. 2003, 103, 4131-4146.
    • (2003) Chem. Rev , vol.103 , pp. 4131-4146
    • Adam, W.1    Krebs, O.2
  • 10
    • 33646419797 scopus 로고    scopus 로고
    • For recent reviews on nitroso Diels-Alder reactions (NDA), see: Y. Yamamoto, H. Yamamoto, Eur. J. Org. Chem. 2006, 2031-2043;
    • For recent reviews on nitroso Diels-Alder reactions (NDA), see: Y. Yamamoto, H. Yamamoto, Eur. J. Org. Chem. 2006, 2031-2043;
  • 22
    • 0141763802 scopus 로고    scopus 로고
    • for recent enantioselective NDA reactions, see: j X. Ding, Y. Ukaji, S. Fujinami, K. Inomata, Chem. Lett. 2003, 32, 582-583;
    • for recent enantioselective NDA reactions, see: j) X. Ding, Y. Ukaji, S. Fujinami, K. Inomata, Chem. Lett. 2003, 32, 582-583;
  • 31
    • 37049138823 scopus 로고
    • For perbenzoic acid, see: b
    • For perbenzoic acid, see: b) Y. Yost, H. R. Gutmann, J. Chem. Soc. C 1970, 2497-2499;
    • (1970) J. Chem. Soc. C , pp. 2497-2499
    • Yost, Y.1    Gutmann, H.R.2
  • 33
    • 34548800550 scopus 로고    scopus 로고
    • 5), see: d) H. Caro, Angew. Chem. 1898, 10, 845-846;
    • 5), see: d) H. Caro, Angew. Chem. 1898, 10, 845-846;
  • 43
    • 34548808304 scopus 로고    scopus 로고
    • [6d,9c,9e]
    • [6d,9c,9e]
  • 44
    • 0001196233 scopus 로고
    • For recent review, see
    • For recent review, see: P. Zuman, B. Shah, Chem. Rev. 1994, 94, 1621-1641.
    • (1994) Chem. Rev , vol.94 , pp. 1621-1641
    • Zuman, P.1    Shah, B.2
  • 46
    • 0344442699 scopus 로고    scopus 로고
    • Recent reviews for selenium-catalyzed oxidation of organic compounds, see: a
    • Recent reviews for selenium-catalyzed oxidation of organic compounds, see: a) J. Mlochowski, M. Brzaszcz, M. Giurg, J. Palus, H. Wojtowicz, Eur. J. Org. Chem. 2003, 22, 4329-4339;
    • (2003) Eur. J. Org. Chem , vol.22 , pp. 4329-4339
    • Mlochowski, J.1    Brzaszcz, M.2    Giurg, M.3    Palus, J.4    Wojtowicz, H.5
  • 48
    • 0035819724 scopus 로고    scopus 로고
    • 2 as terminal oxidant, see: c G.-J. ten Brink, B. C. M. Fernandes, M. C. A. van Vliet, I. W. C. E. Arends, R. A. Sheldon, J. Chem. Soc. Perkin Trans. 1 2001, 224-228 (epoxidation reaction of alkenes);
    • 2 as terminal oxidant, see: c) G.-J. ten Brink, B. C. M. Fernandes, M. C. A. van Vliet, I. W. C. E. Arends, R. A. Sheldon, J. Chem. Soc. Perkin Trans. 1 2001, 224-228 (epoxidation reaction of alkenes);
  • 52
    • 0000133367 scopus 로고    scopus 로고
    • dehydrogenation of carbonyl compounds
    • D. Crich, G. R. Barba, Org. Lett. 2000, 2, 989-991 (dehydrogenation of carbonyl compounds);
    • (2000) Org. Lett , vol.2 , pp. 989-991
    • Crich, D.1    Barba, G.R.2
  • 53
    • 0001340751 scopus 로고    scopus 로고
    • S.-I. Murahashi, T. Shiota, Tetrahedron Lett. 1987, 28, 2383-2386 (oxidation of secondary amines);
    • g) S.-I. Murahashi, T. Shiota, Tetrahedron Lett. 1987, 28, 2383-2386 (oxidation of secondary amines);
  • 54
    • 27644563193 scopus 로고    scopus 로고
    • oxidation of imine to oxaziridine
    • h) B. H. Brodsky, J. Du Bois, J. Am. Chem. Soc. 2005, 127, 15391-15393 (oxidation of imine to oxaziridine).
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 15391-15393
    • Brodsky, B.H.1    Du Bois, J.2
  • 55
    • 34548744268 scopus 로고    scopus 로고
    • 2. In the latter case only 25% conversion of aniline was achieved after 2 h to give azo compound as the main product (no nitroso compound could be detected.).
    • 2. In the latter case only 25% conversion of aniline was achieved after 2 h to give azo compound as the main product (no nitroso compound could be detected.).
  • 58
    • 84982077928 scopus 로고    scopus 로고
    • [4e]
    • [4e]
  • 59
    • 4243068287 scopus 로고    scopus 로고
    • [4e]
    • [4e]
  • 64
    • 34548802148 scopus 로고    scopus 로고
    • The one-pot strategy with the addition of all components from the beginning was also tried in our system, but almost no target oxazines <5, could be observed despite the full consumption of the aniline substrate after 2 h of reaction. It was supposed that the conjugated dienes react with selenium catalyst to generate non-active selenium species and thus retard the catalytic oxidation reaction of aniline under the one-pot reaction conditions
    • The one-pot strategy with the addition of all components from the beginning was also tried in our system, but almost no target oxazines (<5%) could be observed despite the full consumption of the aniline substrate after 2 h of reaction. It was supposed that the conjugated dienes react with selenium catalyst to generate non-active selenium species and thus retard the catalytic oxidation reaction of aniline under the one-pot reaction conditions.
  • 66
    • 0041073683 scopus 로고
    • b) J. Firl, Chem. Ber. 1968, 101, 218-225;
    • (1968) Chem. Ber , vol.101 , pp. 218-225
    • Firl, J.1
  • 69
    • 0025998222 scopus 로고    scopus 로고
    • [16a]
    • [16a]


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.