Martin's sulfurane
Martin's sulfurane is the organosulfur compound with the formula Ph2S[OC(CF3)2Ph]2 (Ph = C6H5). It is a white solid that easily undergoes sublimation. The compound is an example of a hypervalent sulfur compound called a sulfurane. As such, the sulfur adopts a see-saw structure, with a lone pair of electrons as the equatorial fifth coordinate of a trigonal bipyramid, like that of sulfur tetrafluoride (SF4).[1] The compound is a reagent in organic synthesis. One application is for the dehydration of a secondary alcohol to give an alkene:[2]
- RCH(OH)CH2R' + Ph2S[OC(CF3)2Ph]2 → RCH=CHR' + Ph2SO + 2 HOC(CF3)2Ph
![](../I/Martin_sulfurane_mechanism.png.webp)
Mechanism of the dehydration using Martin's sulfurane.
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Names | |
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Preferred IUPAC name
Bis[(1,1,1,3,3,3-hexafluoro-2-phenylpropan-2-yl)oxy]diphenyl-λ4-sulfane | |
Identifiers | |
3D model (JSmol) |
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ChemSpider | |
ECHA InfoCard | 100.156.587 |
EC Number |
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PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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Properties | |
C30H20F12O2S | |
Molar mass | 672.53 g·mol−1 |
Appearance | white solid |
Melting point | 107–109 °C (225–228 °F; 380–382 K) |
Hazards | |
GHS labelling: | |
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Danger | |
H314 | |
P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references |
References
- Martin, J. C.; Arhart, R. J.; Franz, J. A.; Perozzi, E. F.; Kaplan, L. J. "Bis[2,2,2-trifluoro-1-phenyl-1-(trifluoromethyl)ethoxy]diphenyl sulfurane". Organic Syntheses. 57: 22. doi:10.15227/orgsyn.057.0022.
- Roden, Brian A. (2001). "Diphenylbis(1,1,1,3,3,3-hexafluoro-2-phenyl-2-propoxy)sulfurane". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rd409. ISBN 0471936235.
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