Martin's sulfurane
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Preferred IUPAC name Bis[(1,1,1,3,3,3-hexafluoro-2-phenylpropan-2-yl)oxy]diphenyl-λ4-sulfane | |
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3D model (JSmol) |
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ChemSpider |
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ECHA InfoCard | 100.156.587 |
EC Number |
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PubChem CID |
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UNII |
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CompTox Dashboard (EPA) |
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InChI
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Properties | |
Chemical formula | 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: | |
Pictograms | |
Danger | |
Hazard statements | H314 |
Precautionary statements | 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 |
Chemical compound
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
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.
- v
- t
- e
disulfides
- Al2S3
- As2S2
- As2S3
- As2S5
- As4S4
- Au2S
- Au2S3
- B2S3
- BaS
- BeS
- Bi2S3
- CS2
- C3S2
- C6S6
- CaS
- CdS
- CeS
- CoS
- Cr2S3
- CSSe
- CSTe
- CuFeS2
- CuS
- D2S
- Dy2S3
- Er2S3
- EuS
- FeS2
- GaS
- H2S
- HfS2
- HgS
- In2S3
- K2S
- LaS
- LiS
- MgS
- MoS2
- MoS3
- NaHS
- Na2S
- NH4HS
- NiS
- P4Sx
- PbS
- PbS2
- PSCl3
- PSI3
- PtS
- ReS2
- Re2S7
- SiS
- SrS
- TlS
- VS
- SeS2
- S2U
- WS2
- WS3
- Sb2S3
- Sb2S5
- Sb4S3O3
- Sm2S3
- Y2S3
- ZrS2
- La
2O
2S - Gd
2O
2S
- S2Br2
- SBr2
- S2Cl2
- SCl2
- SCl4
- SF2
- SF4
- S2F10
- SF6
- S2I2
and oxyhalides
- SO2
- SO3
- SOBr2
- SOCl2
- SOF2
- SOF4
- H2S3O6
- H2SO3
- H2SO4
- H2S2O7
- H2SO5
Sulfites |
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Sulfates |
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- C2H4S
- C2H6S3
- C4H4S
- C32H66S2
- CHCl3S
- C2H3SN