Reactivities of Stable Rotamers. XXXVIII. Reaction of Chlorine with 1-(9-Fluorenyl)-2-(1-methylethenyl)naphthalene Rotamers: Outstanding Solvent Effects on Product Distribution and Ritter Type Reactions in Acetonitrile

Reactions of the olefinic moiety of the title compounds with chlorine were done as carbon tetrachloride, nitromethane, and acetonitrile solutions. The ap-isomer afforded a mixture of the corresponding addition product and olefins that are derived by deprotonation of the intervening chloro-carbocation. The product distribution was strongly affected by the solvents, although chlorinated olefins are the main products in carbon tetrachloride. The sp-isomer yielded the chloro-olefins that are rotationally isomeric with these compounds in carbon tetrachloride. No cyclized compound, which is expected if the attack of the intermediate cation on a benzene ring closely located to it takes place, was detected under these conditions. By contrast, the reaction in nitromethane resulted in formation of the cyclized compound as a major product from the sp isomer. In acetonitrile, the reaction afforded the cyclized compound in a fair yield from the sp, but that of the ap isomer gave products that were derived by the Ritte...