TRANSITION METAL CATALYZED REARRANGEMENT OF DIMETHYL VINYLCYCLOBUTENE DICARBOXYLATES DERIVATIVES TO DIMETHYL CYCLOHEXADIENE DICARBOXYLATES AND PHTHALATES

by Lovchik, Martin Alan

Vinylcyclobutene derivatives rearrange in the presence of transition metals to form cyclohexadienes and phthalates. Previous work in our group showed that this rearrangement could be performed with Ni(l), Ti(lll), Fe(ll), and Sm(ll). For this thesis, a large variety of metals was studied for these rearrangements. In addition, these methods were applied to various derivatives of vinylcyclobutene. It was found that Pd(ll) would promote the rearrangement to yield phthalates, in the same manner as Ti(lll) and Sm(ll). In addition, a new type of rearrangement was found. Methyl dereivatives of vinylcyclobutene, bearing a methyl substituent on the vinyl group, rearranged to form cyclopentadienes. X-Ray crystallography was used to prove the structure of the dimethyl derivative of vinylcyclobutene. The structures of the other synthesized compounds were confirmed by various spectroscopic analyses.