Selectfluor as a nucleofuge in the reactions of azabicyclo[n.2.1]alkane beta-halocarbamic acid esters (n = 2,3)

ORGN 289

Kevin C. Cannon, kcc10@temple.edu, Department of Chemistry, Temple University, 130 Beury Hall, 13th street, Philadelphia, PA 19122
The ability of Selectfluor to act as a nucleofuge for hydrolysis of beta-anti-halides was investigated with N-alkoxycarbonyl derivatives of 6-anti-X-7-anti-Y-2-azabicyclo[2.2.1]heptanes and 4-anti-X-8-anti-Y-6-azabicyclo[3.2.1]octanes. The azabicycles contained X = I or Br groups in the methanobridge and Y = F, Br, Cl, or OH substituents in the larger bridge. The relative reactivities of the halides were a function of the azabicycle, the halide and its bridge, and the addition of Selectfluor or mercuric fluoride as a nucleofuge. All halide displacements occurred with retention of stereochemistry. Selectfluor with sodium bromide or sodium chloride competitively oxidized some haloalcohols to haloketones.
 

Heterocycles and Aromatics
8:00 AM-11:40 AM, Tuesday, April 8, 2008 Morial Convention Center -- Rm. R06, Oral

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008