Martin's sulfurane

Martin's sulfurane
Names
Preferred IUPAC name
Bis[(1,1,1,3,3,3-hexafluoro-2-phenylpropan-2-yl)oxy]diphenyl-λ4-sulfane
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.156.587 Edit this at Wikidata
EC Number
  • 628-306-5
UNII
  • 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
  • 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
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:
GHS05: Corrosive
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).

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
Mechanism of the dehydration using Martin's sulfurane.

References

  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. ISBN 0471936235.