No abstract

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

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