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Phenyllithium is an organometallic agent with the empirical formula C 6 H 5 Li. It is most commonly used as a metalating agent in organic syntheses and a substitute for Grignard reagents for introducing phenyl groups in organic syntheses. [ 3 ]
tert-Butyllithium, with three weakly electron donating alkyl groups, is the strongest base commercially available (pKa = 53). As a result, the acidic protons on −OH, −NH and −SH are often protected in the presence of organolithium reagents.
Those with five organic substituents are rare, although P(C 6 H 5) 5 is known, being derived from P(C 6 H 5) 4 + by reaction with phenyllithium. [citation needed] Phosphorus ylides are unsaturated phosphoranes, known as Wittig reagents, e.g. CH 2 P(C 6 H 5) 3. These compounds feature tetrahedral phosphorus(V) and are considered relatives of ...
The erythro betaine can be converted to the threo betaine using phenyllithium at low temperature. [18] This modification affords the E-alkene. The Schlosser variant of the Wittig reaction. Allylic alcohols can be prepared by reaction of the betaine ylide with a second aldehyde. [19] For example: An example of the Schlosser variant of the Wittig ...
Phenyl radical group. In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula C6H5, and is often represented by the symbol Ph (archaically φ) or Ø.
Thiophenol is an organosulfur compound with the formula C 6 H 5 SH, 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, where the oxygen atom in the hydroxyl group (-OH) bonded to the aromatic ring in phenol is replaced by a sulfur atom.
Here, phenyllithium 1 attacks the carbonyl group of DMF 2, giving tetrahedral intermediate 3. Because the dimethylamide anion is a poor leaving group, the intermediate does not collapse and another nucleophilic addition does not occur. Upon acidic workup, the alkoxide is protonated to give 4, then the amine is protonated to give 5.
A general acyl group (blue) in a ketone (top left), as an acylium cation (top centre), as an acyl radical (top right), an aldehyde (bottom left), ester (bottom centre) or amide (bottom right).