I. Synthesis of substituted naphthalenes utilizing active nickel. II. Synthesis of substituted naphthoquinones and formation of a charge transfer complex. III. Synthesis of substituted 1,4-diphenyl-2-butenes from (eta(6):eta(6)-1,4-diphenyl-1,3-butadiene)-bis(tricarbonylchromium)

Active nickel-mediated cycloaddition of fumaronitrile, diethyl fumarate, or maleic anhydride with 5,6-disubstituted-$\alpha,\alpha\sp\prime$-dibromo-3,6-dimethoxy-o-xylene gave substituted tetrahydronaphthalenes in good yields. Substitution on the 5,6 positions of the o-xylene were bromo, cyano, and hydro. Conversion of the substituted tetrahydronaphthalenes to the fully aromatic naphthalenes was accomplished in very good to excellent yields. Oxidation of 2,3-dicyano-5,8-dimethoxynaphthalene gave 6,7-dicyano-1,4-naphthoquinone in good yield. Bromination gave 2,3-dibromo-6,7-dicyano-1,4-naphthoquinone which had a stable reduction potential close to TCNQ. A charge transfer complex of 2,3-dibromo-6,7-dicyano-1,4-naphthoquinone and tetrathiofulvalene was formed in acetonitrile. Reduction of ($\eta\sp6$:$\eta\sp6$-1,4-diphenyl-1,3-butadiene)bis-(tricarbonylchromium) with two moles of lithium naphthalide produced a stable dianion. Treatment of the dianion with electrophiles, followed by oxidative cleavage of the two tricarbonylchromium groups, yielded 1,4-disubstituted-1,4-diphenyl-2-butenes. Yields were from fair to very good, with increased yields from use of HMPA as a co-solvent. Electrophiles included primary and secondary alkyl halides, alkyl halides with remote cyano and carboethoxy functionality, and benzaldehyde