THE ACYLOIN REACTION USING TETHERED DIESTERS

A study of the intramolecular acyloin condensation using diesters teth ered by their alkoxide groups was undertaken. The goal was to provide a method for optimizing the yield of mixed acyloin products from the r eaction of two different esters by utilizing tethered dissimilar ester s as substrates. The results of the study show that the yield of the a cyloin condensation is dependant on the tether length. Tethers of 8 an d 14 carbons in length give yields comparable to those obtained from a n intermolecular control reaction while shorter tethers give reduced y ields of product. However, the use of mixed tethered diesters and a cr ossover experiment between two different tethered substrates provides a statistical distribution of products. These observations have been i nterpreted as resulting from a fragmentation of the initially formed r adical anion intermediate that destroys the tethered nature of the sub strate(s).