Oxidation of 1??hydroxyazetidines to four??membered cyclic nitrones and β??lactams

PA van Elburg, DN Reinhoudt

Index: Elburg, P. A. van; Reinhoudt, D. N. Recueil des Travaux Chimiques des Pays-Bas, 1988 , vol. 107, # 5 p. 381 - 387

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Abstract

Abstract The 1-(benzyloxy) azetidines 7a-c and 16a, b were synthesized by reductive cyclization of the corresponding oximes 5a-c and 14a-d. Oxidation of the 1- hydroxyazetidines 8a-c and 17 with PbO 2 afforded the corresponding four-membered cyclic nitrones 18a-c and the bicyclic four-membered nitrones 18d and 18e, which were characterized as the cycloadducts 19a-c and 20 by reaction with dimethyl ...