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Synthesis 1997; 1997(3): 309-312
DOI: 10.1055/s-1997-1181
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An Improved Method for Preparation of Nitrile Oxides from Nitroalkanes for In Situ Dipolar Cycloadditions

Yochai Basel, Alfred Hassner*
  • *Department of Chemistry, Bar-Ilan University, Ramat-Gan 52900 Israel
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Publication History

Publication Date:
31 December 2000 (online)

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A new method has been found for generation of nitrile oxides in situ from nitroalkanes under mild conditions. Thus, reaction of nitroalkanes 1 with di-tert-butyl dicarbonate (2) and 4-dimethyl-aminopyridine (3) as catalyst in the presence of dipolarophiles at room temperature afforded cycloadducts (e.g. 5,6, and 7) in improved yields compared to known methods. Solvent effects were also noted.

Generation of nitrile oxides from nitroalkanes using (BOC)2O and DMAP is disclosed.

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