Oxidation of N-hydroxyazetidines: A novel synthesis of N-acetoxy β-Lactams and four-membered cyclic nitrones

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Pennings, M.L.M. and Reinhoudt, D.N. (1982) Oxidation of N-hydroxyazetidines: A novel synthesis of N-acetoxy β-Lactams and four-membered cyclic nitrones. Tetrahedron Letters, 23 (9). pp. 1003-1006. ISSN 0040-4039

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Abstract:The N-hydroxyazetidines 2 and 3 are prepared startinfrom 2,3-dihydroazete 1-oxides (1a and 1b 0 by reduction with sodium borohydride and by reaction with a nucleophile, respectively. The N-thydroxyazetidines 2 and 3 can be oxidized with mercury (II) oxide to the corresponding nitrones 1 ; oxidation of the N-hydroxyazetidine 2a (unsubstituted at C-4) with two equivalent of lead tetraacetate tyields the N-tacetoxy β-lactam 4.
Item Type:Article
Copyright:© 1982 Elsevier Science
Link to this item:http://purl.utwente.nl/publications/68930
Official URL:http://dx.doi.org/10.1016/S0040-4039(00)87005-7
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