46%), and 2-nonyne (36%) by glpc analysis. These were separated by glpc and identified by infrared and nmr.Partial Reduction of Phenylpropadiene.-Phenylpropadiene (1.16 g, 0.01 mol) was reduced with 0.23 g (0.01 g-atom) of sodium in 50 ml of liquid ammonia. The reaction product was stirred for 3 hr and worked up in the usual manner.The glpc analysis of the product (0.95 g) showed the presence of n-propylbenzene (17.2%), propenylbenzene (22.5%), 1-phenylpropyne (56.8%), and an unidentified product (3.5%). The first three components were separated by glpc and identified by nmr. When the reaction in another lot was arrested and worked up after just 15 min, the product analysis showed 15.7% ra-propylbenzene, 19.5% allylbenzene, and 64.8% 1-phenylpropyne.Reduction of Phenylpropadiene with Equivalent Quantity of Sodium.-Phenylpropadiene (1.16 g, 0.01 mol) in dry ether was added into a solution of 0.46 g (0.02 g-atom) of sodium in 50 ml of liquid ammonia. The reaction mixture was stirred only for The Journal of Organic Chemistry 15 min and worked up in the usual way. The product (0.92 g) analysis by glpc showed the presence of w-propylbenzene (21.9%), allylbenzene (15.3%), and 1-phenylpropyne (62.8%). These were separated and identified by nmr.
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