Desaurin

General structure of desaurins
2,4-Dimethylidene-1,3-dithietane
Names
IUPAC name
2,4-dimethylidene-1,3-dithietane
Identifiers
3D model (JSmol)
  • parent: InChI=1S/C4H4S2/c1-3-5-4(2)6-3/h1-2H2
    Key: QWWVTCYHWDEKBZ-UHFFFAOYSA-N
  • parent: C=C1SC(=C)S1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Desaurins are a type of sulfur-containing heterocycle. The parent is 2,4-bismethylene-1,3-dithietane. They are derived from the base-promoted condensation of carbon disulfide with "active methylene" compounds:[1]

2 Z2CH2 + 2 CS2 → Z2C=CS2C=CZ2 + 2 H2S

According to X-ray crystallography, the C4S2 core of desaurins is planar.[2] With unsymmetrical substitution (at the ends of the methylene groups), they can exist as separable cis and trans isomers.

References

  1. ^ Yates, Peter; Moore, Donald R.; Lynch, Thomas R. (1971). "Carbon Disulfide. II. Reaction with Active Methylene Compounds. The Structures of the Desaurins". Canadian Journal of Chemistry. 49 (9): 1456–1466. doi:10.1139/v71-238.
  2. ^ Selzer, Tzvia; Rappoport, Zvi (1996). "Bis(dimesitylmethylene)-1,3-dithietane, -1,2,4-trithiane, and -1,2,4,5-tetrathiane. Conformation and DNMR Study. Observable Dimesityl Thioketene". The Journal of Organic Chemistry. 61 (21): 7326–7334. doi:10.1021/jo960911k. PMID 11667658.
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