NOTES 593 plets centered at 4.75 and 4.63 ppm (>C=CH2), a singlet at 2.16 ppm (-CH&=), a broad singlet at 1.77 ppm (ring protons), a broad partially resolved singlet at 1.62 ppm (CHaC=), and a singlet at 1.43 ppm (-0-H). Anal. Calcd for C10H160: C, 78.90; H , 10.59. Found: I I C, 79.07; H, 10.53.PreDaration of Isobutvlmaenesium Ch1oride.l1-Mamesium turnin'gs (1.17 g, 0.048 g-itomj were placed in the reaction flask, and after the system had been swept with dry nitrogen for several minutes, a solution of 0.18 g (0.002 mole) of isobutyl chloride in 10 ml of sodium-dried ether was added. Initiation of the reaction was effected by the addition of several drops of ethyl bromide followed by warming on a water bath. To the moderately stirred mixture was added a solution of 4.44 g (0.048 mole) of isobutyl chloride in 25 ml of sodium-dried ether at a rate such that gentle refluxing was maintained. Stirring was continued for 2 hr after the addition of halide had been completed, and the reaction mixture was allowed to stand overnight.Reaction of Isobutylmagnesium Chloride with A2-Cyclohexenone.12-To the above suspension was added, in turn, 50 mg (0.51 mmole) of freshly prepared cuprous chloride,* and a solution of 1.92 g (0.020 mole) of A2-cyclohexenone in 50 ml of sodiumdried ether. After employing the previously described isolation procedure, gas chromatographic analysiss of the crude reaction mixture revealed the presence of alcohol VI (35%) and ketone VI1 (63y0, components listed in order of increasing retention time). The remainder of the product mixture (2%) was material of lower volatility which was not characterized.A pure sample of the alcohol VI,9 n25~ 1.4708, exhibits infrared absorption10 at 3625 (unassociated 0-H) and 1645 cm-l (cis CH=CH). The nmr spectrumlo of the sample has a singlet at 5.54 ppm (-CH=CH-), a broad singlet at 1.64 ppm (ring protons), a doublet at 1.41 and 1.33 ppm (-CH&H<), a singlet a t 1.27 ppm (-0-H), and a doublet at 0.97 and 0.88 ppm [-CH-(CHO)PI. Anal. Calcd for CloHlsO: C, 77.87; H, 11.76. Found: C, 77.98; H, 11.87. A pure sample of the ketone VII,g n Z 4 3~ 1.4527 (lit.E n Z 5~ 1.4525), exhibits infrared absorptionlo at 1715 cm-l (C-0). The nmr spectrum10 of the sample has a broad multiplet centered at 1.81 ppm (ring protons) and a doublet at 0.91 and 0.81 ppm [-CH(CHi)zl. Anal. Calcd for CloHlsO: C, 77.87; H, 11.76. Found: C, 77.72; H, 11.95.In the absence of cuprous chloride, gas chromatographic analysis9 of the crude reaction mixture revealed the presence of alcohol VI (9770) and ketone VI1 (3%, components listed in order of increasing retention time).(11) The apparatus was identical with that used for the preparation of (12) The procedure was identical with that for the reaction of @-methyl-B-methylallylmagnesium chloride. allylmagnesium chloride with As-cyclohexenone.The present work was initiated with the desire of obtaining 1,2,2,3,4,5hexachloro -4cyclopentene-1 ,3dicarboxylic acid (11) by oxidative ozonolysis' of 1,2,3,4,7,7-hexachlorobicyclo [2.2.1]-2,5-heptadiene (I).(1) For ...