(Aminomethyl)polystyrene-HF complexes: Application as efficient acid catalysts and fluorinating agents

ORGN 147

G. K. S. Prakash, gprakash@usc.edu1, Kevin Glinton, glinton@usc.edu1, Thomas Mathew, tmathew@usc.edu1, Chiradeep Panja, chiradep@usc.edu1, V. Prakash Reddy, preddy@umr.edu2, Pierre M. Esteves, pesteves@iq.ufrj.br3, and George A. Olah, olah@usc.edu1. (1) Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, 837 Bloom Walk, Los Angeles, CA 90089-1661, (2) Department of Chemistry, University of Missouri-Rolla, Rolla, MO 65409, (3) Physical Chemistry Group, Universidade Federal do Rio de Janeiro, Instituto de Química, Cidade Universitária CT Bloco A, Rio de Janeiro, Brazil
(Aminomethyl)polystyrene is found to act as an efficient reservoir for anhydrous HF minimizing the risk associated with its handling. We found that it can form ionic solid HF complexes with varying amounts of anhydrous HF. The solid can be used as a convenient source for fluorination of alcohols under mild conditions. However, treatment of 1-adamantanemethanol with the reagent results in its ring expansion to homoadamantane. Reactions with various alcohols will be discussed.
 

Physical Organic Chemistry, Combinatorial and Process Chemistry, New Reactions and Methodology, Peptides, Proteins and Amino Acids
8:00 PM-10:00 PM, Sunday, April 6, 2008 Morial Convention Center -- Hall A, Poster

Division of Organic Chemistry

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