Conversion of N-Acyl-4-acyloxy-β-lactams into 1,3-Oxazin-6-ones: Two Consecutive Pseudopericyclic Processes
Organic Letters2000Vol. 2(7), pp. 965–968
Citations Over TimeTop 10% of 2000 papers
Abstract
N-Acyl-4-acyloxy-beta-lactams are converted into 1,3-oxazin-6-ones under basic conditions. This transformation is believed to proceed via N-acylazetones, which rearrange to the final products by a sequence of two electrocyclic processes. The calculated (RHF and B3LYP) transition structures of both concerted reactions are shown to present characteristic pseudopericyclic orbital topologies.
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