
%0 Journal Article
%A Cox, Matthew 
%A Dixon, Michael 
%A Lister, Troy 
%A Prager, Rolf H. 
%T Intramolecular Interactions in Carbenes Derived During the Pyrolysis of <emph type="3">N</emph>-Alkenylisoxazolones
%J Australian Journal of Chemistry
%D 2004/05/06
%V 57
%N 5
%P 455-460
%K 
%R https://doi.org/10.1071/CH03154
%U https://www.publish.csiro.au/paper/CH03154 
%X Flash vacuum pyrolysis of ethyl 3-(3-methyl-5-oxo-2,5-dihydroisoxazole-2-yl)-3-phenylpropenoate yields 4-ethoxy-3-hydroxy-2-methyl-5-phenylpyridine in addition to the expected pyrrole. The structure assignment is based on two-dimensional NMR and computational evidence. The pyrolysis of the corresponding dimethyl amide gives a mixture of three 3-hydroxypyridines, in addition to the pyrrole. Evidence is presented for the formation of intermediate 1,4-oxazepines by a six-electron electrocyclic reaction of a carbene with ester or amide carbonyl groups. 
