Date of Award
Bachelor of Science
Previous studies on the reaction of the optically active organotin, diallylisopropylmyrtanyltin, to produce homoallylic alcohols, using boron trifluoride as a Lewis acid, produced racemic mixtures regardless of the aldehyde used.1 In this experiment bromine was attached to the tin atom in allylmyrtanylphenyltin bromide, letting tin become an internal Lewis acid. Benzaldehyde was reacted with this compound to see it a single optically active product could be synthesized. After the alcohol had been separated out using vacuum distillation, the optical rotation of the product was taken and showed no appreciable rotation; thus a racemic mixture was produced.
Drew, Simon Paul, "Chirality transfer in the synthesis of homoallylic alcohols" (1987). Honors Theses. 2010.