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Synthesis 2006(10): 1635-1638  
DOI: 10.1055/s-2006-926440
PAPER
© Georg Thieme Verlag Stuttgart · New York

Simple Preparation of O-Substituted Hydroxylamines from Alcohols

Sébastien Albrecht, Albert Defoin*, Céline Tarnus
Laboratoire de Chimie Organique et Bioorganique, UMR 7015, École Nationale Supérieure de Chimie de Mulhouse, Université de Haute-Alsace, 3 rue Alfred Werner, 68093 Mulhouse Cédex, France
Fax: +33(3)89336875 ; e-Mail: A.Defoin@uha.fr;
Further Information

Publication History

Received 23 December 2005
Publication Date:
11 April 2006 (online)

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Abstract

A direct preparation of O-substituted hydroxylamines from alcohols is described by O-alkylation of tert-butyl N-hydroxy­carbamate with the methanesulfonates of respective alcohols, followed by acidic N-deprotection.

Key words

amination - nucleophilic substitution - hydroxylamine

    References

  • 1 Adamczyk M. Reddy RE. Synth. Commun.  2001,  41:  579 
    Google Scholar
  • 2 Kim D.-K. Gam J.-S. Kim Y.-W. Lim J.-S. Kim H.-T. Kim KH. J. Med. Chem.  1997,  40:  2363 
    CrossrefPubMedGoogle Scholar
  • 3a Nicolaus BJR. Pagani G. Testa E. Helv. Chim. Acta  1962,  45:  1381 
    Google Scholar
  • 3b Nicolaus BJR. Pagani G. Testa E. Helv. Chim. Acta  1962,  45:  1393 
    Google Scholar
  • 3c See also: Zeeh B. Metzger H. Methoden zur Herstellung und Umwandlung von Hydroxylaminen, In Houben-Weyl, Methoden der Organischen Chemie   Müller E. Thieme Verlag; Stuttgart: 1971.  Vol. X-1:  p.1184 ff 
    Google Scholar
  • 4 Zeeh B. Metzger H. Methoden zur Herstellung und Umwandlung von Hydroxylaminen, In Houben-Weyl, Methoden der Organischen Chemie   Müller E. Thieme Verlag; Stuttgart: 1971.  Vol. X-1:  p.1183 ff 
    Google Scholar
  • 5 Zeeh B., Metzger H.; Methoden zur Herstellung und Umwandlung von Hydroxylaminen, In Houben-Weyl, Methoden der Organischen Chemie; Müller E., Thieme Verlag: Stuttgart, 1971; Vol. X-1, 1192 ff
  • 6 Grochowski E. Jurczak J. Synthesis  1976,  682 
    Article in Thieme ConnectGoogle Scholar
  • 7 Jones DS. Hammaker JR. Tedder ME. Tetrahedron Lett.  2000,  41:  1531 
    CrossrefGoogle Scholar
  • 8 Gabriel S. Ber Dtsch. Chem. Ges.  1887,  20:  2224 
    CrossrefGoogle Scholar
  • 9 Ing HR. Manske RHF. J. Chem. Soc.  1926,  2348 
    CrossrefGoogle Scholar
  • 10 Foot OF. Knight DW. Chem. Commun.  2000,  975 
    CrossrefGoogle Scholar
  • 11 Theilacker W. Ebke K. Angew. Chem.  1956,  68:  303 
    Google Scholar
  • 12 Hight A. Prior T. Bell RA. Rangachari PK. J. Pharmacol. Exp. Ther.  1999,  288:  490 
    PubMedGoogle Scholar
  • 13 Behr JB. Chevrier C. Defoin A. Tarnus C. Streith J. Tetrahedron  2003,  59:  543 
    CrossrefGoogle Scholar
  • 14 Burns DH. Miller JD. Chan H.-K. Delaney MO. J. Am. Chem. Soc.  1997,  119:  2125 
    CrossrefGoogle Scholar
  • 15 Bly RS. Mateer RA. Tse K.-K. Veazey RL. J. Org. Chem.  1973,  38:  1518 
    CrossrefGoogle Scholar
  • 16 Dennison PhR. Gibson A. Gray AIG. Patrick L. J. Chem. Soc., Perkin Trans. 1  1997,  721 
    CrossrefGoogle Scholar
  • 17 Choudary BM. Chowdari NS. Naidu S. Kantam ML. Tetrahedron  2000,  56:  7291 
    CrossrefGoogle Scholar
  • 18 Fischli A. Müller PM. Helv. Chim. Acta  1980,  63:  1619 
    CrossrefGoogle Scholar
  • 19 Schumann EL. Heinzelman RV. Greig ME. Veldkamp W. J. Med. Chem.  1964,  7:  329 
    CrossrefPubMedGoogle Scholar
  • 20 Macchia M. Menchini E. Nencetti S. Orlandini E. Rosello A. Belfiore MSt. Il Farmaco  1996,  51:  255 
    Google Scholar
  • 21 Mavunkel BJ. Rzeszotarski WJP. Kaplita V. DeHaven-Hudkins DL. Eur. J. Med. Chem.  1994,  29:  659 
    CrossrefGoogle Scholar
  • 22 Choong I. Ellman JA. J. Org. Chem.  1999,  64:  6528 
    CrossrefPubMedGoogle Scholar
  • 23 Ishikawa T. Kamiyama K. Matsunaga M. Tawada H. Iizawa Y. Okonogi K. Miyake A. J. Antibiot.  2000,  53:  1071 
    CrossrefPubMedGoogle Scholar