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With a suitably chosen copper catalyst and solvent [e.g., a suspension of copper(1) oxide in 2,4,6-collidine], the reduction of aryl halides, ArHal -w ArH, was achieved in substantial yield by means of sodium alkoxides derived from a variety of primary, secondary, and tertiary alcohols ; the corresponding aldehyde or ketone was in some cases also isolated. In the absence of catalyst, reduction occurred, though less effectively, with some of the alkoxides. The corresponding alcohols had little or no reactivity. Effects of varying the halide (including the use of an or-bromo-ketone), solvent, and copper species are reported, together with comparative experiments involving hydride-ion donors (sodium hydride, borohydride, formate) as reductants.COMPETITION between reductive and nucleophilic sub-Similar competitive effects were later encountered in stitution by rnethoxide ion, as shown in (l), was ob-copper-promoted reactions of halides with other nucleoserved in an earlier study of copper-promoted reactions philes, such as phenols and amines.l of aryl halides (Ar being l-naphthyl, and the yields of In certain cases, competitive reduction has also been ether and hydrocarbon being 45% and 50% respectively) : observed when alkoxides were intended to cause

9)* Spectra were determined at 100 Mc./sec. in ca. 5 % solutions in carbon tetrachloride. When spectra were determined in deuterochloroform, similar results were obtained but at slightly lower 7-values (TO-0.15).