Abstract
Fluorine substituents have been observed to have a remarkable effect upon the rate and stereochemical outcome of the butadiene-cyclobutene thermal conrotatory 4π-electron electrocyclic interconversion. The substituent effects observed in this system and in other pericyclic systems have enhanced one's understanding of the mechanisms of such reactions, such that only a small probable effect of fluorine substituents was predicted for the related 6π-electron system, i.e., the disrotatory 1,3,5-hexatriene-1,3-cyclohexadiene conversion. In an attempt to probe this system, a strategy was devised which would utilize the thermolysis of 1,2-bis(trifluorovinyl)naphthalene
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