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Synthesis 1997; 1997(6): 657-660
DOI: 10.1055/s-1997-1393
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Stereoselective Synthesis of N-Hydroperoxyalkyloxaziridines: A New Class of Heterocyclic Hydroperoxides

M. Rosaria Iesce* , Flavio Cermola, Antonio Guitto
  • *Dipartimento di Chimica Organica e Biologica dell’Università di Napoli Federico II, via Mezzocannone 16, I-80134 Napoli, Italy, Fax +39(81)5521217
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Publication Date:
31 December 2000 (online)

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Irradiation of hydroperoxynitrones 3, which can be easily prepared by dye-sensitized photooxygenation of 2-methoxyfuran (1) in the presence of oximes 2, leads to the highly functionalized trans-oxaziridines 4. The reaction proceeds smoothly at room temperature in fairly good yields.

2-methoxyfuran - hydroperoxyalkyloxaziridines - hydroperoxynitrone - photoisomerization - oxime

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