Desaurin

2,4-Dimethylidene-1,3-dithietane
Names
	IUPAC name 2,4-dimethylidene-1,3-dithietane
Identifiers
3D model (JSmol)	parent: Interactive image;
PubChem CID	parent: 129652735;
	InChI parent: InChI=1S/C4H4S2/c1-3-5-4(2)6-3/h1-2H2 Key: QWWVTCYHWDEKBZ-UHFFFAOYSA-N;
	SMILES 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). Infobox references

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

^ 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.
^ 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.

[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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