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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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Chemical Compound Review: 

HOPHT     2-hydroxyisoindole-1,3-dione

Synonyms: Phthaloxime, NHPI, SureCN1410, PubChem17315, NSC-770, ...
 
 
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High impact information on NSC770

  • A solid-phase approach based on the alkylation by alcohols of a new supported N-hydroxyphthalimide reagent using a Mitsunobu reaction followed by methylaminolysis has been optimized [1].
  • PINO was generated in CH(3)CN by reaction of N-hydroxyphthalimide (NHPI) with Pb(OAc)(4) or, for the kinetic study of the most reactive substrates (X = OMe, OPh), with tert-butoxyl radical produced by 266 nm laser flash photolysis of di-tert-butyl peroxide [2].
  • Thus, dialkyl hydroxylamines have O-H bond strengths of only ca. 70 kcal/mol, while acylhydroxylamines and N-hydroxyphthalimide (NHPI), containing two acyl substituents at nitrogen, are characterized by BDE values of ca. 80 and 88 kcal/mol, respectively [3].
  • [reaction: see text] Screening combinations of five catalyst precursors with 13 phosphorus ligands identified cyclization catalysts that favor carbocyclization-trapping with N-hydroxyphthalimide over a competing cycloisomerization mode [4].
  • A comprehensive structural characterization of the colorless and yellow forms of N-hydroxyphthalimide (NHP), the deuterated form (NDP), and the ethoxylated form (ethoxy-NHP) has been carried out using single-crystal X-ray diffraction, FTIR and Raman spectroscopies, and scanning electron microscopy [5].

References

  1. A new supported reagent for the parallel synthesis of primary and secondary O-alkyl hydroxylamines through a base-catalyzed Mitsunobu reaction. Maillard, L.T., Benohoud, M., Durand, P., Badet, B. J. Org. Chem. (2005) [Pubmed]
  2. Electron-transfer mechanism in the N-demethylation of N,N-dimethylanilines by the phthalimide-N-oxyl radical. Baciocchi, E., Bietti, M., Gerini, M.F., Lanzalunga, O. J. Org. Chem. (2005) [Pubmed]
  3. Hydroxylamines as oxidation catalysts: thermochemical and kinetic studies. Amorati, R., Lucarini, M., Mugnaini, V., Pedulli, G.F., Minisci, F., Recupero, F., Fontana, F., Astolfi, P., Greci, L. J. Org. Chem. (2003) [Pubmed]
  4. Controlling mode selectivity in palladium-catalyzed bisdiene carbocyclizations: optimizing for cyclization-trapping over cycloisomerization. Takacs, J.M., Schroeder, S.D., Han, J., Gifford, M., Jiang, X.T., Saleh, T., Vayalakkada, S., Yap, A.H. Org. Lett. (2003) [Pubmed]
  5. Elusive forms and structures of N-hydroxyphthalimide: the colorless and yellow crystal forms of N-hydroxyphthalimide. Reichelt, H., Faunce, C.A., Paradies, H.H. The journal of physical chemistry. A (2007) [Pubmed]
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