A coupling reaction or oxidative coupling in organic chemistry is a catch-all for a range of reactions in Organometal... between a ketoneKetone
A ketone is either the functional group characterized by a carbonyl group linked to two other carbon atoms or a chemical co... and a thioketoneThioketone
Thioketones are organic compounds that are the sulfur-containing analogues of ketones.... through a diazoDiazo
Diazo refers to a type of organic compound that has the general forumula R2C=N2.... intermediate forming an alkeneAlkene
In organic chemistry, an alkene, olefin, or olefine is an unsaturated chemical compound containing at least one ... .
This reaction has been pioneered by Hermann StaudingerHermann Staudinger
German chemist Hermann Staudinger discovered a chemical reaction known as the Staudinger reaction.... and therefore the reaction also goes by the name Staudinger type diazo-thioketone coupling.
In chemistry, a reaction mechanism is the step by step sequence of elementary reactions by which overall chemical change occ... for this reaction the diazoDiazo Summary
Diazo refers to a type of organic compound that has the general forumula R2C=N2.... compound is a 1,3-dipoleFacts About 1,3-dipole
A 1,3-dipole is a type of organic compound with a three-atom pi-electron system containing 4 electrons delocalized over thre... which reacts with the thioketoneThioketone Overview
Thioketones are organic compounds that are the sulfur-containing analogues of ketones.... in a 1,3-dipolar cycloaddition1,3-dipolar cycloaddition
The 1,3-dipolar cycloaddition, also known as the Huisgen cycloaddition or Huisgen reaction, is an organic chem... to a thiadiazoline. This intermediate is unstable and through nitrogen gas expulsion and formation of an intermediate thiocarbonyl ylide it forms a stable episulfideEpisulfide
An episulfide is a three membered saturated heterocycle containing two carbon atoms and one sulfur atom.... . TriphenylphosphineTriphenylphosphine
Triphenylphosphine is a common organophosphorus compound with the formula P3 - often abbreviated to PPh3 or Ph3P.... opens the three-membered ring and then forms a sulfaphosphatane in a manner similar to the Wittig reactionWittig reaction
The Wittig reaction is a chemical reaction of an aldehyde or ketone with a triphenyl phosphonium ylide to give an alkene and... . In the final step triphenylphosphinesulfoxide is expulsed liberating the alkeneAlkene Summary
In organic chemistry, an alkene, olefin, or olefine is an unsaturated chemical compound containing at least one ... .
Scope
The diazo compound can be obtained from a ketoneKetone
A ketone is either the functional group characterized by a carbonyl group linked to two other carbon atoms or a chemical co... by reaction with hydrazineHydrazine
Hydrazine is the chemical compound with formula N2H4.... to a hydrazoneHydrazone
A hydrazone is a class of organic compounds with the structure R2C=NNR2.... followed by oxidation. Many reagents exist for this conversion for example silver(I) oxideSilver(I) oxide
Silver oxide, also known as silver rust and argentous oxide, is a chemical compound with formula 2 and CAS numbe... and (bis(trifluoroacetoxy)iodo)benzene(Bis(trifluoroacetoxy)iodo)benzene
right|150pxright|150px|benzenebenzene is a hypervalent iodine compound used as a reagent in organic chemistry.... . The thioketoneThioketone
Thioketones are organic compounds that are the sulfur-containing analogues of ketones.... required for this reaction can be obtained from a ketone and phosphorus pentasulfidePhosphorus pentasulfide
Phosphorus pentasulfide, also called phosphorus sulfide, 'sulfur phosphide, 'diphosphorus pentasulfide and '... . Desulfurization of the episulfide can be accomplished by many phosphines and also by copperCopper
Copper is a chemical element in the periodic table that has the symbol Cu and atomic number 29.... powder.
The main advantage of this reaction over the McMurry reactionMcMurry reaction
The McMurry reaction is an organic reaction in which two ketone or aldehyde groups are coupled to an alkene in the presence ... is the notion that the reaction can take place with two different ketones. In this regard the diazo-thioketone coupling is a cross-coupling rather than a homocoupling.
