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SOME REACTIONS OF METHANESULFINYL CHLORIDE 805 160°/16 mm.; n2¿ 1.6112. On redistillation, through a 30cm. Fenske ring-packed column at a reflux ratio of 1:10, the product obtained possessed the following constants: b.p. 135-137°/4 mm.; n2Ds 1.6110; 1.1040.3-Isopropylidene-3-pentenenitrile9 (VIII). Acetone was condensed with 3-pentenenitrile in the same manner as described above for benzaldehyde. The product was distilled through a 76-cm. Nester spinning band column at a reflux ratio of 1:10. The liquid product melted at -8°. The compound added oxygen readily, and it was stored under nitrogen prior to analysis. Low results, particularly for carbon, were obtained until it was discovered that the analytical sample had to be burned very slowly.The compound showed infrared absorption at 3.4µ for saturated CH, 3.5µ for unsaturated CH, 4.5µ for conjugated nitrile, 6.17µ for conjugated unsaturation, 7.25µ for CH3, and 10.45µ for a trans internal double bond.2-Isopropylidene-3-pentenenitrile proved difficult to hydrolyze. In contrast with 3-pentenenitrile, no acid or lactone formed when it was boiled with concentrated hydrochloric acid. The nitrile was hydrolyzed by boiling two days with 17% aqueous sodium hydroxide. On acidification and distillation, about 10% of 3-pentenoic acid and about 10% of crude liquid 2-isopropylidene-3-pentenoic acid were recovered. Following a procedure employed by Whyte and Cope10 to hydrolyze hindered nitriles, 48 g. of 2-isopropylidene-3-pentenenitrile was stirred 15 hr. at reflux temperature with a mixture of 45 g. of potassium hydroxide, 20 g. of water, and 100 ml. of diethylene glycol. After acidification and fractional distillation, 1.7 g. of a straw-colored liquid

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