Studies with Bicyclo[2,2,2]octenes. III. Adducts of 2,3-dihydrobenzyl alcohol and its acetate with ethyl acrylate

Abstract

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.