
%0 Journal Article
%A Botica, I 
%A Mirrington, RN 
%T Studies with Bicyclo[2,2,2]octenes. III. Adducts of 2,3-dihydrobenzyl alcohol and its acetate with ethyl acrylate
%J Australian Journal of Chemistry
%D 1971/07/01
%V 24
%N 7
%P 1467-1480
%K 
%R https://doi.org/10.1071/CH9711467
%U https://www.publish.csiro.au/paper/CH9711467 
%X The structures and stereochemistry of the Diels-Alder adducts of 2,3- dihydro-benzyl alcohol (1a) and its acetate (1b) with ethyl acrylate have been established.     The directing effect of the hydroxymethyl group in (1a) was such that 82% ?ortho? and 18% ?meta? adducts were obtained. The reaction of ethyl acrylate with 2,3-dihydrobenzyl acetate (1b) was slower than with (1a) but gave a similar proportion of meta adduct (21%).     Numerous attempts to prepare lactone (9) by an intramolecular Diels-Alder reaction with 2,3-dihydrobenzyl acrylate (1c) were unsuccessful. 
