Novel chemistry of oxoammonium salts

ORGN 109

Priya P. Pradhan,, William F. Bailey,, and James M. Bobbitt, Department of Chemistry, University of Connecticut, 55 North Eagleville Road, Storrs, CT 06269
Oxoammonium salts, most commonly employed for selective oxidation of alcohols, display other interesting chemistry as well (for a review, see: Org. Prep. Proc. Int. 2004, 36, 1). Our efforts in this area have focused on investigation of the utility of 4-acetamido-2,2,6,6-tetramethylpiperidin-1-oxoammonium tetrafluoroborate (1), an inexpensive, readily prepared, thermally stable oxidant. The oxidation of alcohols or diols with 1, conducted in tandem with further transformations obviating the need to isolate small or unstable aldehyde or ketone products will be discussed, as will the scope and limitations of novel electrophilic additions of 1 to electron-rich alkenes