Quantitative ring contraction of 5-hydroxy-1,3-oxazin-2-ones into 5-hydroxymethyl-1,3-oxazolidin-2-ones: A DFT study

The ring contraction of trans-5-hydroxy-1,3-oxazin-2-ones 1 into cis-5-hydroxymethyl-oxazolidinones 3 was studied with different bases and nucleophiles and it was found that it is the basicity and not the nucleophilicity the factor responsible for the ring contractions. A DFT study was made for the proposed mechanism.