Abstract
The reaction of cyclopentadienylcopper dimethyl sulfide with 1,8-diiodonaphthalene provides a method for coupling cyclopentadienyl groups to the naphthalene nucleus. The product formed by coupling of two such groups in peri positions on the naphthalene ring is the Diels-Alder adduct 3. Deuterium labeling experiments have been carried out which show that this product is formed through conversion of the initial 1-iodo-8-(5-cyclopentadienyl)naphthalene (9) to 1,8-di(5-cyclopentadienyl)-naphthalene (10). This, in turn, undergoes a single sigmatropic [1.5] hydrogen shift to give 1-(1-cyclopentadienyl)-8-(5-cyclopentadienyl)naphthalene (11), which collapses to the Diels-Alder adduct 3
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