Martin's sulfurane

Last updated
Martin's sulfurane
MartinSulfurane.svg
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 628-306-5
PubChem CID
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
Appearancewhite solid
Melting point 107–109 °C (225–228 °F; 380–382 K)
Hazards
GHS labelling:
GHS-pictogram-acid.svg
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. Martin sulfurane mechanism.png
Mechanism of the dehydration using Martin's sulfurane.

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In chemistry, a dehydration reaction is a chemical reaction that involves the loss of water from the reacting molecule or ion. Dehydration reactions are common processes, the reverse of a hydration reaction.

<span class="mw-page-title-main">Oxalyl chloride</span> Chemical compound

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<span class="mw-page-title-main">Triphenylphosphine</span> Chemical compound

Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C6H5)3 and often abbreviated to PPh3 or Ph3P. It is widely used in the synthesis of organic and organometallic compounds. PPh3 exists as relatively air stable, colorless crystals at room temperature. It dissolves in non-polar organic solvents such as benzene and diethyl ether.

Organosulfur compounds are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur derivatives, e.g., saccharin. Nature abounds with organosulfur compounds—sulfur is vital for life. Of the 20 common amino acids, two are organosulfur compounds, and the antibiotics penicillin and sulfa drugs both contain sulfur. While sulfur-containing antibiotics save many lives, sulfur mustard is a deadly chemical warfare agent. Fossil fuels, coal, petroleum, and natural gas, which are derived from ancient organisms, necessarily contain organosulfur compounds, the removal of which is a major focus of oil refineries.

<span class="mw-page-title-main">Periodinane</span>

Periodinanes also known as λ5-iodanes are organoiodine compounds with iodine in the +5 oxidation state. These compounds are described as hypervalent because the iodine center has more than 8 valence electrons.

<span class="mw-page-title-main">Thiophenol</span> Chemical compound

Thiophenol is an organosulfur compound with the formula C6H5SH, sometimes abbreviated as PhSH. This foul-smelling colorless liquid is the simplest aromatic thiol. The chemical structures of thiophenol and its derivatives are analogous to phenols. An exception is the oxygen atom in the hydroxyl group (-OH) bonded to the aromatic ring is replaced by a sulfur atom. The prefix thio- implies a sulfur-containing compound and when used before a root word name for a compound which would normally contain an oxygen atom, in the case of 'thiol' that the alcohol oxygen atom is replaced by a sulfur atom.

<span class="mw-page-title-main">Sulfur tetrafluoride</span> Chemical compound

Sulfur tetrafluoride is the chemical compound with the formula SF4. It is a colorless corrosive gas that releases dangerous HF upon exposure to water or moisture. Despite these unwelcome characteristics, this compound is a useful reagent for the preparation of organofluorine compounds, some of which are important in the pharmaceutical and specialty chemical industries.

<span class="mw-page-title-main">Iodine monochloride</span> Chemical compound

Iodine monochloride is an interhalogen compound with the formula ICl. It is a red-brown chemical compound that melts near room temperature. Because of the difference in the electronegativity of iodine and chlorine, this molecule is highly polar and behaves as a source of I+.

<span class="mw-page-title-main">Diphenyl disulfide</span> Chemical compound

Diphenyl disulfide is the chemical compound with the formula (C6H5S)2. This colorless crystalline material is often abbreviated Ph2S2. It is one of the more commonly encountered organic disulfides in organic synthesis. Minor contamination by thiophenol is responsible for the disagreeable odour associated with this compound.

<span class="mw-page-title-main">Phenylboronic acid</span> Chemical compound

Phenylboronic acid or benzeneboronic acid, abbreviated as PhB(OH)2 where Ph is the phenyl group C6H5-, is a boronic acid containing a phenyl substituent and two hydroxyl groups attached to boron. Phenylboronic acid is a white powder and is commonly used in organic synthesis. Boronic acids are mild Lewis acids which are generally stable and easy to handle, making them important to organic synthesis.

<span class="mw-page-title-main">Diethylaminosulfur trifluoride</span> Chemical compound

Diethylaminosulfur trifluoride (DAST) is the organosulfur compound with the formula Et2NSF3. This liquid is a fluorinating reagent used for the synthesis of organofluorine compounds. The compound is colourless; older samples assume an orange colour.

<span class="mw-page-title-main">Triphenylphosphine sulfide</span> Chemical compound

Triphenylphosphine sulfide is the organophosphorus compound with the formula (C6H5)3PS, usually written Ph3PS. It is a colourless solid, which is soluble in a variety of organic solvents.

Iodane generally refers to any organic derivative of iodine. Without modifier, iodane is the systematic name for the parent hydride of iodine, HI. Thus, any organoiodine compound with general formula RI is a substituted iodane. However, as used in the context of organic synthesis, the term iodane more specifically refers to organoiodine compounds with nonstandard bond order of bonds between iodine and other atoms, i.e., bond order of iodine greater than 1, making this term a synonym for hypervalent iodine. These iodine compounds are hypervalent because the iodine atom formally contains more than the 8 electrons in the valence shell required for the octet rule. When iodine is ligated to an organic residue and electronegative ligands, hypervalent iodine occurs in a +3 oxidation state as iodine(III) or λ3-iodane, or in a +5 oxidation state as iodine(V) or λ5-iodane, or in a +7 oxidation state as iodine(VII) or λ7-iodane. Here, lambda convention is used to give the nonstandard bond order.

<span class="mw-page-title-main">Organobismuth chemistry</span>

Organobismuth chemistry is the chemistry of organometallic compounds containing a carbon to bismuth chemical bond. Applications are few. The main bismuth oxidation states are Bi(III) and Bi(V) as in all higher group 15 elements. The energy of a bond to carbon in this group decreases in the order P > As > Sb > Bi. The first reported use of bismuth in organic chemistry was in oxidation of alcohols by Frederick Challenger in 1934 (using Ph3Bi(OH)2). Knowledge about methylated species of bismuth in environmental and biological media is limited.

<span class="mw-page-title-main">Phenyl isocyanate</span> Chemical compound

Phenyl isocyanate is an organic compound typically abbreviated PhNCO. The molecule consists of a phenyl ring attached to the isocyanate functional group. It is a colourless liquid that reacts with water. Phenyl isocyanate has a strong odor and tearing vapours, therefore it has to be handled with care.

<span class="mw-page-title-main">Jones oxidation</span> Oxidation of alcohol

The Jones oxidation is an organic reaction for the oxidation of primary and secondary alcohols to carboxylic acids and ketones, respectively. It is named after its discoverer, Sir Ewart Jones. The reaction was an early method for the oxidation of alcohols. Its use has subsided because milder, more selective reagents have been developed, e.g. Collins reagent.

<span class="mw-page-title-main">Phenyl(trichloromethyl)mercury</span> Chemical compound

Phenyl(trichloromethyl)mercury is an organomercury compound with the formula C6H5HgCCl3. It is a white solid that is soluble in organic solvents. The compound is used as a source of dichlorocarbene, e.g. in cyclopropanation reactions, illustrated with tetrachloroethylene as a substrate, the product being hexachlorocyclopropane:

(Chloromethylene)triphenylphosphorane is the organophosphorus compound with he formula Ph3P=CHCl (Ph = phenyl). It is a white solid but is usually generated and used in situ as a reagent in organic synthesis. It is structurally and chemically related to methylenetriphenylphosphorane.

Hydroxymethylation is a chemical reaction that installs the CH2OH group. The transformation can be implemented in many ways and applies to both industrial and biochemical processes.

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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.