Meta-substituted benzene rings and Cope rearrangements via cascade reactions

ORGN 569

Thomas M. Mitzel, Thomas.Mitzel@mail.trincoll.edu and Claire Lawlor, Claire.Lawlor@trincoll.edu. Department of Chemistry, Trinity College, 300 Summit Street, Hartford, CT 06106
Previous studies in our laboratory have shown that allyl-indium metal organometallic complexes add 1,2- to propargyl aldehydes. Studies have also shown that these systems may rearrange via a Cope pathway to give an alpha, beta-unsaturated aldehyde as shown in Scheme 1. In an effort to increase the efficiency of the Cope rearrangement, 1,3-dihalopropene moieties were utilized as nucleophilic species in the system. Introduction of the dihalo species resulted in the formation of a substituted benzene structure when NMF was chosen as the solvent. These reactions, along with the mechanistic pathways of their formation,will be discussed.