Tuesday, 24 May 2005
464

This presentation is part of: Graduate Posters

Neighboring Group Participation in the Syntheses and Reactions of 4-X-exo-8-anti-Iodo-6-azabicyclo[3.2.1]octanes (X=F, Cl, OH). Selectfluor and Mercuric Fluoride as Nucleofuges

Deepa Rapolu1, Grant Krow1, Ryan A. Centafont1, and Kevin C. Cannon2. (1) Temple University, Philadelphia, PA, (2) Penn State Abington, Abington, PA

Stereoselective syntheses of novel 4-exo-8-anti-difunctionalized-6-azabicyclo[3.2.1]octanes containing anti-iodo in the methanobridge and exofluoro, chloro, hydroxy substituents in the other larger bridge have been carried out by reaction of Selectfluor and mercuric fluoride with the appropriate halide. Retention of configuration was observed in all displacement reactions. Precursor halides were synthesized by addition/rearrangement of dihalides or halohydrins to N-alkoxycarbonyl-6-azabicyclo[2.2.2]oct-5-enes.

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