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Primary amine diazeniumdiolate ions of structure {RNN(O)NOR '}(-) as ambident nucleophiles

  1. Author:
    Bohle, D. S.
    Keefer, L. K.
    Saavedra, J. E.

  2. Author Address

    Bohle, D. Scott] McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada. [Keefer, Larry K.] NCI, Frederick, MD 21702 USA. [Saavedra, Joseph E.] NCI, Basic Sci Program, SAIC Frederick Inc, Frederick, MD 21702 USA.
    1. Year: 2009
  2. Journal: Tetrahedron Letters
    1. 50
    2. 43
    3. Pages: 5917-5919
  4. Type of Article: Article
  1. Abstract:

    An O-2-substituted primary amine diazeniumdiolate RHN-N(O)=NOR' is ionized to an anion that attacks an electrophile R '' X via either of two nitrogens to form both RR '' N-N(O)=NOR' and R-N=N(O)-N(R '')OR'. The bidentate character of such anions should be kept in mind when planning or evaluating drug discovery efforts involving diazeniumdiolates of structure RHN-N(O)=NOR'. (C) 2009 Elsevier Ltd. All rights reserved.

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  2. DOI: 10.1016/j.tetlet.2009.08.012
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