DE-O-BENZYLATION OF STERICALLY HINDERED BENZYL ETHERS[1]

Abstract

Sterically hindered benzyl ethers that cannot be removed by hydrogenolysis with a variety of catalysts are removed readily by the reaction with N-bromosuccinimide and light in the presence of aqueous calcium carbonate, a reaction developed by Binkley and Hehemann. It was found that these conditions are compatible with the presence of phthalimides and glycosyl sulfides and fluorides, in addition to the groups previously shown to be inert.

ACKNOWLEDGMENTS

We thank Drs. L. R. Ramaley and J. S. Grossert for accurate mass determinations and D. Johnston and M. Safatli for preparation of some starting materials. We are grateful for financial support from NSERC.