The solution was stirred for 1 hr. at room temperature, and after this time, 100 ml. of absolute methanol was added and the resulting solution was stirred for 2 days, again at room temperature. An equal volume of water was added and the mixture was shaken. The organic phase was washed with sodium bicarbonate solution, then twice with water. The solution was dried over magnesium sulfate and filtered, and the solvent was evaporated under reduced pressure leaving an orange oil. Upon addition of anhydrous ether and subsquent cooling at 0" for 1 day, 1.98 g. of a white crystalline material was obtained. After further evaporation of the solvent and cooling, another 0.30 g. of this material was isolated: m.p. 77-78', 2.28 g. (50%).Anal. Calcd. for C2oH1SBrC1203: C, 52.88; H, 3.32. Found: C, 52.55; H, 3.32. The n.m.r. spectrum indicated that the product was 2,2-di-(o-chlorobenzoyl)-6-bromocyclohexanone. There was a multiplet at 5.1 p.p.m., corresponding to one hydrogen, and aromatic and aliphatic areas in a ratio of 8 to 6. The infrared spectrum showed a carbonyl stretch a t 5.73 and 6.03 p ; A : : " 245 mp ( E 14,700).Polarographic Reduction of 6,6-Di(o-Chlorobenzoyl)-l-morpholinocyclohexene-1 . -A M solution of this dibenzoylated enamine in acetonitrile, with t-butylammonium iodide as supporting electrolyte, was reduced using a dropping mercury cathode and mercury pool anode. The resulting polarogram indicated a reduction of the dibenzoylated enamine ( E l / z = -1.36 v.). A M solution of 1-morpholinocyclohexene-1 showed no reduction under the same conditions. A Sargent Model XXI instrument was used: range, 0-2.5 v.; sensitivity, 0.100 pa./mm.; damping, 2.The Attempted Reaction of 6,6-Di( o-chlorobenzoy1)-1-morpholinocyclohexene-1 with Sodium Borohydride in Ethanol.-To 0.80 g. (0.021 mole) of sodium borohydride in 250 ml. of absolute ethanol, was added 4.40 g. (0.01 mole) of the dibenzoylated enamine and the mixture was stirred for 1 day. After this time it was noticed that some of the enamine had not gone into solution. As a result, 100 ml. of anhydrous tetrahydrofuran was added to increase the solubility. The solution was then stirred for 4 days at room temperature. After this time the solvents were evaporated a t reduced pressure leaving a solid residue. The solid was dissolved in anhydrous methanol, and upon cooling in an ice bath, 3.20 g. of a white solid was isolated. A mixture melting point with the starting material showed no depression (149-151'). An infrared spectrum was identical with that of the starting material. (The 3.20 g. of solid corresponds to a recovery of 72y0.) An infrared spectrum of the oil which remained did not give any evidence of a reaction. As with the starting material, there was a carbonyl peak a t 5.7 p .Monobenzoylated cyclohexanones (as the copper chelates) were isolated after hydrolysis of the oily residue remaining when the dibenzoylated enamines were crystallized and removed from the reaction of the benzoyl chlorides with l-morpholinocyclohexene-1. After hydrolysis, the organic ...
