Martin's sulfurane

Martin's sulfurane
Names
	IUPAC name bis[(1,1,1,3,3,3-hexafluoro-2-phenylpropan-2-yl)oxy]-diphenyl-λ4-sulfane
Identifiers
CAS Number	32133-82-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	2843600;
ECHA InfoCard	100.156.587
EC Number	628-306-5;
PubChem CID	3608068;
UNII	F9631K90E5;
CompTox Dashboard (EPA)	DTXSID90394127;
	InChI InChI=1S/C30H20F12O2S/c31-27(32,33)25(28(34,35)36,21-13-5-1-6-14-21)43-45(23-17-9-3-10-18-23,24-19-11-4-12-20-24)44-26(29(37,38)39,30(40,41)42)22-15-7-2-8-16-22/h1-20H Key: RMIBJVUYNZSLSD-UHFFFAOYSA-N;
	SMILES C1=CC=C(C=C1)C(C(F)(F)F)(C(F)(F)F)OS(C2=CC=CC=C2)(C3=CC=CC=C3)OC(C4=CC=CC=C4)(C(F)(F)F)C(F)(F)F;
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 pictograms
GHS Signal word	Danger
GHS hazard statements	H314
GHS precautionary statements	P260, P264, P280, P301+330+331, P303+361+353, P304+340, P305+351+338, 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

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.

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[1] 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.

[2] 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.