This research focuses on the use of organophosphorus chemistry related to the Wittig olefin synthesis to develop practical reagents for the conversion of aldehydes into E-alkenes. The origin of solvent effects on ester-stabilized ylides will be studied and probes for detecting electron transfer pathways in the Wittig process will be developed. The potential for use of chiral phosphines as nucleophilic catalysts for entioselective transformations will also be tested. In other areas, Dr. Vedejs will explore the thermodynamic advantage of 1,3-dienes relative to allenes as a driver for the Cope rearrangement and studies will focus on understanding the role of heteroatoms on the stereochemistry of alkene osmylation and epoxidation reactions. %%% With this Accomplishment Based renewal award, the Synthetic Organic Program is supporting the research of Dr. Edwin Vedejs of the Department of Chemistry at the University of Wisconsin, Madison. Professor Vedejs will focus his work on mechanistic and preparative studies of the Wittig reaction, a widely-used route to the preparation of alkenes which are straight chain compounds with double bonds, an extremely important class of organic compounds.