Distillation of 3.6 g. of the crude mixture afforded the following fractions: (1) b.p. 25°( 30 mm.), 0.15 g.; (2) b.p. 24°( 0.15 mm.), 0.8 g.; (3) 24-26°( 0.15 mm.), 1.7 g.; (4) 26°( 0.15 mm.), 0.5 g.; and residue, 0.4 g., viscous oil.The fractions -were characterized by g.l.c. and n.m.r. spectroscopy. Fraction 1 consisted of 70% of 3-propenethiol and 30% of its dimer V; fraction 2 consisted of 87% of 1,3-propanedithiol and 13% of 3-propenethiol; fraction 4 consisted mainly of 1,3propanedithiol; the residue showed a S-H band at 3.94 µ in the infrared. The n.m.r, spectrum in CS2 showed the following characteristic signals: multiplet, = 1.88 (center methylene group of -CH2CH2CH2-), and multiplet, 2.78 p.p.m. (methylene groups attached to sulfur in S-CH2CH2CH2-S). Preparation of Trimethylene Disulfide "Dimer." 19-To a solution of 10.8 g. (0.1 mole) of 1,3-propanedithiol, and 100 mg.(0.0013 mole) of -butyl amine in 50 ml. of methanol, 10 g. (0.11 mole) of /-butyl hydroperoxide was added within 30 min. The fully acknowledged.
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