Carbomethoxymethylenetriphenylphosphorane is a

chemical A chemical substance is a unique form of matter with constant chemical composition and characteristic properties. Chemical substances may take the form of a single element or chemical compounds. If two or more chemical substances can be combin ...

compound used in

organic Organic may refer to: * Organic, of or relating to an organism, a living entity * Organic, of or relating to an anatomical organ Chemistry * Organic matter, matter that has come from a once-living organism, is capable of decay or is the product ...

syntheses. It contains a

phosphorus Phosphorus is a chemical element; it has Chemical symbol, symbol P and atomic number 15. All elemental forms of phosphorus are highly Reactivity (chemistry), reactive and are therefore never found in nature. They can nevertheless be prepared ar ...

atom bound to three

phenyl group In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula , and is often represented by the symbol Ph (archaically φ) or Ø. The phenyl group is closely related to benzene and can be viewed as a benzene ...

s, and doubly bound to the alpha position of

methyl acetate Methyl acetate, also known as MeOAc, acetic acid methyl ester or methyl ethanoate, is a carboxylate ester with the formula CH3COOCH3. It is a flammable liquid with a characteristically pleasant smell reminiscent of some glues and nail polish remo ...

. It undergoes a

Wittig reaction The Wittig reaction or Wittig olefination is a chemical reaction of an aldehyde or ketone with a triphenyl phosphonium ylide called a Wittig reagent. Wittig reactions are most commonly used to convert aldehydes and ketones to alkenes. Most o ...

. It is used in the

Vitamin B12 total synthesis The total synthesis of the complex biomolecule vitamin B12, vitamin B12 was accomplished in two different approaches by the collaborating research groups of Robert Burns Woodward at Harvard University, Harvard and Albert Eschenmoser at ETH Zuric ...

Production

Carbomethoxymethylenetriphenylphosphorane can be made via a multistep reaction using

bromoacetic acid Bromoacetic acid is a chemical compound with the formula . This colorless solid is a relatively strong alkylating agent. Bromoacetic acid and its esters are widely used building blocks in organic synthesis, for example, in pharmaceutical chemistry ...

dicyclohexylcarbodiimide is an organic compound with the chemical formula (C6H11N)2C. It is a waxy white solid with a sweet odor. Its primary use is to couple amino acids during artificial peptide synthesis. The low melting point of this material allows it to be melte ...

, and

triphenylphosphine Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C6H5)3 and often abbreviated to P Ph3 or Ph3P. It is versatile compound that is widely used as a reagent in organic synthesis and as a l ...

. This makes a

phosphonium In chemistry, the term phosphonium (more obscurely: phosphinium) describes polyatomic cations with the chemical formula (where R is a hydrogen or an alkyl, aryl, organyl or halogen group). These cations have tetrahedral structures. The ...

salt, which is converted to the final product by

sodium carbonate Sodium carbonate (also known as washing soda, soda ash, sal soda, and soda crystals) is the inorganic compound with the formula and its various hydrates. All forms are white, odourless, water-soluble salts that yield alkaline solutions in water ...

in water.

Reactions

Carbomethoxymethylenetriphenylphosphorane reacts with

aldehyde In organic chemistry, an aldehyde () (lat. ''al''cohol ''dehyd''rogenatum, dehydrogenated alcohol) is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred ...

s to give a two carbon atom extension. The carbomethoxymethylene group replaces the oxygen of the aldehyde to give a ''trans-'' double bond.

References

Organophosphorus compounds Esters Phenyl compounds Organic compounds {{Organic-compound-stub