2-H-Methoxyoxete: a reactive intermediate en route to methyl acrylate from methoxyacetylene and formaldehyde under BF3 catalysis. An ab initio HF and DFT study

The formation of methyl acrylate from formaldehyde and methoxyacetylene, and the influence of BF3 as a model Lewis acid are studied by means of ab initio HF and DFT calculations (HF/6-31G∗ and B3LYP/6-31G∗). In both cases calculations are in favour of a pathway involving the asynchronous (or stepwise) formation (the C–C bond being formed first) of the reactive intermediate methoxy oxete, and its further electrocyclic ring-opening into methyl acrylate.