The purpose of this work was the study of synthetic approaches to specifically labeled deuterated 1, 4-dimethylnaphthalenes. Alkylation of ortho- and para-dibromobenzenes eventually led to the formation of some 1, 4-dimethylnaphthalene although deuteration was rather poor. Under the conditions employed, much isomerization of Friedel-Crafts products resulted. Not only did the bromines rearrange intramolecularly, but substantial rearrangement of the alkylating moiety may also have occurred. The major products of these reactions were dibromophenylcyclohexanes. It appears from the products obtained by the methods employed in our work that specific monodeuteration rather than specific dideuteration should be used to attain the desired product
