New applications of electrochemical oxidations and reductions. Selective replacement technology for organic synthesis

ORGN 482

Tomas Hudlicky, Department of Chemistry, Department of Chemistry, University of Florida, PO Box 117200, Gainesville, FL 32611

 

Electrochemical oxidations and reductions are both selective and environmentally benign.  Examples of several types of efficient and selective transformations will be presented. Anodic oxidation of N-acylamines of type 1 provides precursors for acyl iminium cyclizations that are exploited in synthesis of isoquinoline alkaloids.  Reduction of cinnamyl ethers such as 2 or cinnamyl carbamates of type 3 occurs selectively in preference to other allylic systems.  Several examples of such reductions will be disclosed.  In compounds such as 4, it is also possible to selectively reduce either a vinyl halide or cinnamyl ether or both, depending on the conditions selected.  Details and further potential of these results in selective transformations will be presented.

 

 

Synthetic Organic Electrochemistry
9:00 AM-11:30 AM, Wednesday, September 10, 2003 Sheraton New York -- Royal Ballroom A, Oral

Division of Organic Chemistry
The 226th ACS National Meeting, New York, NY, September 7-11, 2003