2-Methylene-1,3-propanedithiol (allyl dithiol) was synthesized according to previously reported procedure (34). In a 1000-ml round-bottom flask with a stir bar, potassium ethyl xanthogenate (56.4 g, 352 mmol) was dissolved into ethanol (500 ml). 3-Chloro-2-(chloromethyl)-1-propene (18.5 ml, 160 mmol) was added dropwise, and the reaction was left overnight. The solids were then removed with filtration, and ethanol was removed using a rotary evaporator. Diethyl ether (200 ml) and water (100 ml) were added to the yellow residue, and the organic phase was removed and washed with water (2×, 100 ml), washed with brine (1×, 100 ml), and dried over sodium sulfate. The ether was removed under a vacuum, resulting in the protected allyl dithiol as a yellow low-viscosity liquid used without further purification in the next step. In a flame-dried, 50-ml round-bottom flask with an addition funnel under argon, the protected allyl dithiol (10 g, 33.8 mmol) was added over 30 min to anhydrous ethylenediamine (16 ml) held at 20°C. After 3 hours, the reaction mixture was slowly added to 200 g of ice and 32 ml of sulfuric acid (concentrated). The milky white solution was extracted with diethyl ether (2×, 200 ml). The organic phases were combined and extracted with 2 M sulfuric acid (2×, 100 ml) and brine (1×, 100 ml). The organic phase was then dried over sodium sulfate, filtered, and concentrated in vacuo, resulting in a slightly yellow low-viscosity liquid with an extremely foul odor. The allyl dithiol was distilled immediately before use (60°C, 0.1 mmHg, 2.6 g, 60% yield). Impurities were observed if allowed to sit overnight after purification. 1H nuclear magnetic resonance (NMR) (400 MHz, CDCl3, 25°C): 4.99 (broad singlet, 2H), 3.37 to 3.34 (multiplet, 4H), 1.48 (triplet, J = 8.15 Hz, 2H).

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