Oxoammonium salts: Ene-like addition to alkenes and other novel chemistry

ORGN 951

James M. Bobbitt, james.bobbitt@uconn.edu, Priya P. Pradhan, priya.pradhan@uconn.edu, William F. Bailey, william.bailey@uconn.edu, Ashley L Bartelson, ashley.bartelson@uconn.edu, and Raymond P Lorenzoni III, raymond.lorenzoni@uconn.edu. Department of Chemistry, University of Connecticut, 55 North Eagleville Road, Storrs, CT 06269
Oxoammonium salts have been used as selective oxidizing agents for alcohols, and they display other interesting chemistry as well (N. Merbouh, J. M. Bobbitt, C. Bruckner, Org. Prep. Proc. Int. 2004, 36, 1). Recent efforts have been focused on investigation of the reactions of salt 1 with alkenes, alcohols, and amines. As shown below, 1 adds selectively, and in high yield, to isolated tri-substituted alkenes in an ene-like fashion. Novel oxidation reactions of 1 with alcohols and amines will also be discussed. An overall mechanism for oxoammonium salt oxidations will be suggested.

 

New Reactions and Methodology
1:00 PM-5:00 PM, Thursday, 14 September 2006 Moscone Center -- Room 133, Oral

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006