Deprotection of aromatic ethers using solid support acids as reagents

ORGN 137

Vanessa Amanda Guzman, vanessaguzman9985@gmail.com, Department of Chemistry, Stanford University, 333 Campus Drive, Mudd Building, Room 121, Stanford, CA 94305
p-Toluene sulfonic acid (PTS-Si) immobilized on silica has been investigated for its use in the selective debenzylation of aromatic ethers. PTS-Si was found to effectively cleave select ethers over other ethers contained on the same ring based on their position adjacent to chelating groups. Our studies show that this chelation effect influences selectivity regardless of the stability of the carbocation that should form after CO bond cleavage.

 

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