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Isotopic analysis by mass spectrometry proved to be difficult, as the sample underwent back exchange while in the ion source. Rapid analysis indicated that the product consisted of 94 ± 2% diethyl malonate-d2, 6 ± 2% diethyl malonate-cfi, and 0 ± 2% diethyl malonate, though the actual per cent of diethyl malonate-d2 was probably somewhat higher than these figures imply.Reduction of Diethyl Malonate-d2 with Lithium Aluminum Deuteride.-Lithium aluminum deuteride (6.6 g., 0.157 mole) was transferred under anhydrous atmospheric conditions to a 500-ml. three-necked flask containing 250 ml. of ethyl ether freshly distilled from lithium aluminum hydride. The flask was sealed and the deuteride slurry was stirred overnight. In a nitrogen atmosphere a solution of 21.6 g. (0.133 mole) of diethyl malonate-d2 in 30 ml. of ethyl ether (dried as above) was slowly added during a 1.5-hr. period to the lithium aluminum deuteride slurry. After refluxing for 48 hr. in an inert atmosphere, '50 ml. of deuterium oxide was cautiously added to the cooled reaction mixture. The heterogeneous system was refluxed for an additional 2 hr. and then filtered. The residue from the filtration was continuously extracted for 18 hr. with tetrahydrofuran. The organic extracts were combined and the solvents were removed in vacuo.

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