Enhanced O-dealkylation activity of SiCl4/LiI with catalytic amount of BF3

ORGN 641

Daniel Zewge1, Anthony O. King2, Steven Weissman2, and David Tschaen2. (1) Process Research, Merck Research Laboratories, P.O. Box 2000, Rahway, NJ 07065, (2) Department of Process Chemistry, Merck Research Laboratories, P.O.Box 2000, Rahway, NJ 07065
Dibenzyloxydihydrobenzoxathiin 1, which resisted debenzylation with SiCl4/LiI, was effectively debenzylated with SiCl4/LiI in the presence of a catalytic amount of BF3. The HCl salt of the bis-debenzylated product 2 was isolated in 90% yield and 99% purity. This enhanced dealkylation activity has also been observed with other substrates.

 

New Reactions, Methodology, Heterocycles, Aromatics
8:00 PM-10:00 PM, Wednesday, August 25, 2004 Pennsylvania Convention Center -- Hall D, Poster

Division of Organic Chemistry

The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004