γ-chloropropanesulfenyl chloride

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Properties of substance:

γ-chloropropanesulfenyl chloride

Group of substances:

organic

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

C₃H₆Cl₂S

Structural formula as text:

Cl(CH2)3SCl

Molar/atomic mass: 145.046

Synthesis 1:

Reference: Bordwell, F. G., Pitt, B. M. The Formation of α-Chloro Sulfides from Sulfides and from Sulfoxides / Journal of the American Chemical Society. - 1955. - Vol. 77, No. 3 pp. 576 [doi: 10.1021/ja01608a016]

(CH₂)₃S + SO₂Cl₂ → Cl(CH₂)₃SCl + SO₂

A heated solution of 27 g. (0.36 mole) of thiacyclobutane in 80 ml. of pentane containing a crystal of iodine was treated with a solution of 50 g. (0.37 mole) of sulfuryl chloride in 60 ml. of pentane. After approximately half the sulfuryl chloride was added, the mixture gradually developed a bright yellow color. After an additional hour at reflux the mixture was distilled to give 36.5 g. (69%) of a yellow orange liquid, b.p. 64—66° (13 mm ). On standing the sulfenyl chloride rapidly darkened to a black tar with the evolution of hydrogen chloride.

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