Chiroptical Properties of Chiral Acyclic Dienes: Studies in Atropisomerism

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This grant from the Organic Dynamics Program supports the work of Professor Harry M. Walborsky at Florida State University. The chiroptical properties of acyclic 1,3-dienes will be studied. A general method for the preparation of chiral atropisomers of acyclic 1,3-dienes will be devised which utilizes as a key step a cyclopropyl carbinyl rearrangement. The relative and absolute configurations of the chiral 1,3-dienes as well as their chiral precursors will be determined and correlations with various sector rules will be attempted. The rates and activation energies for the thermal racemizations of the dienes will also be established. %%% Compounds which exist as nonsuperimposable mirror images by virtue of hindered rotation about a single bond between two carbon atoms will be examined. A new method for constructing these molecules will be developed. The three dimensional arrangement of the atoms will be determined and the rate at which the two mirror images interconvert will be determined.