ORGN 288 |
Electrophilic activation involving protonated amides
| Douglas A. Klumpp1, Rendy Rendy2, Aaron McElrea2, and Alma Gomez2. (1) Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, IL 60115, (2) Department of Chemistry, California State Polytechnic University, 3801 West Temple Aveune, Pomona, CA 91768 |
The superacid-catalyzed reactions of various amides have been studied. Protonated amide groups are found to participate in two distinctly different modes of electrophilic activation. The protonated amide group can enhance the electrophilic reactivity of an adjacent electrophilic group, like a carboxonium ion (eq 1). Moreover, adjacent cationic groups can themselves increase the electrophilic reactivity of the protonated amide group (eq 2). Reactive dicationic electrophiles can be generated from the appropriate amides, directly observed using low temperature NMR (i.e. dication 1), and exploited in synthetic reactions. The results of these studies will be presented. |
| |
|
Physical Organic, Combinatorial, Materials, Molecular Recognition
8:00 PM-10:00 PM, Tuesday, March 30, 2004 Anaheim Convention Center -- Hall A, Poster
Sci-Mix
8:00 PM-10:00 PM, Monday, March 29, 2004 Anaheim Convention Center -- Hall A, Sci-Mix
Division of Organic Chemistry
The 227th ACS National Meeting, Anaheim, CA, March 28-April 1, 2004
|