cyclohexene sulfide

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Properties of substance:

7-thiabicyclo[4.1.0]heptane

Synonyms:

cyclohexene sulfide

Group of substances:

organic

Empirical formula (Hill's system for organic substances):

C₆H₁₀S

Solubility (g/100 g of solvent):

methanol: soluble [Ref.]

Synthesis 1:

Reference: Snyder, H. R., Stewart, J. M., & Ziegler, J. B. The Synthesis of Amino Mercaptans from Olefin Sulfides / Journal of the American Chemical Society. - 1947. - Vol. 69, No. 11 pp. 2674 [doi: 10.1021/ja01203a033]

To a solution of 130 g. of potassium thiocyanate in 100 ml. of water was added 70 ml. of ethanol and then 60 g. of cyclohexene oxide. This mixture was stirred vigorously for four hours. During this period the temperature rose to 45?°. A 40-g. portion of cyclohexene oxide was added, the mixture was cooled to 20°, and stirred vigorously for an additional twenty hours. The mixture was then saturated with salt and the top layer was separated. The crude sulfide was washed twice with 100-ml. portions of water, dried over magnesium sulfate, and distilled under reduced pressure. The yield was 70 g. (60%, based on the oxide) of clear, colorless liquid boiling at 83—87° at 46 mm.; n(20, D) 1.5292.

Anal. Calcd. for C6H10S: C, 63.0; H, 8.8. Found: C, 62.2; H, 8.6.

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