An investigation of the Pd 2+ mediated rearrangement of trimethylsilyl substituted cycloproplyimine

ORGN 385

Meagan M. Fagan and Banita W. Brown. Department of Chemistry, University of North Carolina at Charlotte, 9201 University City Blvd, Charlotte, NC 28223
This research involves an investigation into the rearrangement of a trimethylsilyl-substituted cyclopropylimine to a substituted pyrrole through a Pd2+ mediated rearrangement. Previously, it has been found that substituted phenylcyclopropylimines successfully rearranged to form pyrrole products through the use of polymeric PdCl2. The reaction below is representative of this rearrangement (Scheme 1).

The electronic effect on the phenyl group influences the stabilization of the rearrangement. In order to further explore the potential applications of the reaction, a trimethylsilyl cyclopropylimine derivative has been prepared, and the proposed rearrangementis being attempted. (Scheme 2)

 

Physical Organic, Materials, Heterocycles, Aromatics, Metal-Mediated Reactions
8:00 PM-10:00 PM, Tuesday, September 9, 2003 Hilton New York -- Americas Hall 1, Poster

Division of Organic Chemistry
The 226th ACS National Meeting, New York, NY, September 7-11, 2003