2-H-methoxyoxete: a reactive intermediate en route to methyl acrylate frommethoxyacetylene and formaldehyde under BF3 catalysis. An ab initio HF andDFT study

The formation of methyl acrylate from formaldehyde and methoxyacetylene, an d the influence of BF3 as a model Lewis acid are studied by means of ab ini tio HF and DFT calculations (HF/6-31G* and B3LYP/6-31G*). In both cases cal culations are in favour of a pathway involving the asynchronous (or stepwis e) formation (the C-C bond being formed first) of the reactive intermediate methoxy oxete, and its further electrocyclic ring-opening into methyl acry late. (C) 2001 Elsevier Science Ltd. All rights reserved.