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Vol. 81 nents under the conditions employed in our experiments were 34, 59, 62, 77 and 95 seconds. The component with the shortest retention time is ketobicyclo[2.2.1]heptane, and the other two major products with retention times of 59 and 62 seconds are believed to be the 1-nitroand 7-nitrobicyclo-[2.2.1]heptanes. The vapor chromatogram showed that these latter two components were present in almost equal concentrations. The retention time for the alkali-soluble 2-nitrobicyclo [2.2.1] heptane under conditions identical to those employed above was 58 seconds. The minor components of the alkali-insoluble product were eluted at retention times of 77 and 95 seconds. In addition to the carbonyl and nitro bands found in the infrared spectrum of this sample a weak doublet at 2.83 and 2.87µ indicated the presence of some hydroxy compound.Nitration of Decahydronaphthalene.-A 207-g. (1.5 moles) sample of decahydronaphthalene (re25o 1.4694) was charged to a 1-liter stainless steel autoclave, pressured to 300 p.s.i.g. and heated to 120°. At this point 34.5 g. (0.75 mole) of nitrogen dioxide dissolved in 100 ml. of carbon tetrachloride (0-5°) was fed into the reaction zone by means of a Milton Roy feed pump. After a total reaction period of 1 hour (50 minutes feed and 10 minutes cook), the autoclave was cooled to room temperature. The reaction mixture was washed first with 150 ml. of water and then extracted with a 5% sodium hydroxide solution for 18 hours. The alkaliinsoluble portion was washed with water and dried over anhydrous magnesium sulfate. Distillation of the dried solution at reduced pressure yielded 122.4 g. (59% recovery) of decahydronaphthalene, b.p. 70°( 14 mm.), 32.1 g. of higherboiling material (re25D 1.4929-1.5010), and a pot residue weighing 16.7 g. The 32.1-g. portion of the distillate was extracted by 130 ml. of 10-15% sodium methoxide for 2.5 hours. The mixture then was diluted with 200 ml. of water, extracted by four 75-ml. portions of diethyl ether, and dried over anhydrous magnesium sulfate. Distillation of the alkaliinsoluble material yielded 10 g. of 9-nitrodecahydronaphthalene, b.p. 60-65°( 0.2 mm.). This amount of product represents a 9.0% yield based on the amount of decahydronaphthalene consumed. The infrared spectrum of the product coincided with that of 9-nitrodecahydronaphthalene which was reported previously.14 Also, the refractive index of the product (re26n 1.4925) was in excellent agreement with that reported in the literature.14-16Acknowledgments.-The author wishes to thank Mr. L. J. Lohr for the interpretation of the infrared spectra and the vapor phase chromatographic work, and Prof. J. D. Roberts for supplying infrared spectra of authentic samples of 2-nitronorbornane and norcamphor.

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