Kinetic isotope effects in the rearrangement of β-acetoxycarbene

CHED 306

Jennifer M. Nguyen, jmnguyen@colby.edu, Martin J. Schnermann, mjschner@scripps.edu, and Dasan M. Thamattoor, dmthamat@colby.edu. Department of Chemistry, Colby College, 5750 Mayflower Hill, Waterville, ME 04901
The rearrangement of β-acetoxycarbene, generated from a non-nitrogenous phenanthrene-based precursor, to the isomeric vinyl acetate was investigated. Three different mechanisms were considered for this process as shown below. Deuterated versions of the carbene were also generated to examine the influence of kinetic isotope effects on the rearrangement pathways.

 

Undergraduate Research Poster Session
2:30 PM-4:30 PM, Monday, August 20, 2007 BCEC -- Exhibit Hall - B2, Poster

Division of Chemical Education

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007