Bridged Azibidines. iii. Lead Tetra-Acetae Oxidation of 5-Aminocycloheptene. Synthesis of Dl-2α-Hydroxytrop Ane

Abstract

5-Aminocycloneptene 3 was oxidized with lead tetraacetate in benzane in the presence of anhydrous potasium carbonate at room tamperature giving the bridged aziridine 4 in ca. 90% yield, this providingand additional example of the new nitrenoid reactionwhich was recently discovered in our laboratory. The aziridine 4 was transformed smoothly intothe 2a-substituted tropanes 13 and 17 and a new synthetic route to these important azacycles was thus established.