Thioanisole is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

with the formula CH₃SC₆H₅. It is a colorless liquid that is soluble in organic solvents. It is the simplest

alkyl In organic chemistry, an alkyl group is an alkane missing one hydrogen. The term ''alkyl'' is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of . A cycloalkyl is derived from a cycloalk ...

–

aryl In organic chemistry, an aryl is any functional group or substituent derived from an aromatic ring, usually an aromatic hydrocarbon, such as phenyl and naphthyl. "Aryl" is used for the sake of abbreviation or generalization, and "Ar" is used as ...

thioether. The name indicates that this compound is the sulfur analogue—the

thioether In organic chemistry, an organic sulfide (British English sulphide) or thioether is an organosulfur functional group with the connectivity as shown on right. Like many other sulfur-containing compounds, volatile sulfides have foul odors. A sul ...

rather than the oxygen-centered

ether In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula , where R and R′ represent the alkyl or aryl groups. Ethers can again be c ...

—of

anisole Anisole, or methoxybenzene, is an organic compound with the formula CH3OC6H5. It is a colorless liquid with a smell reminiscent of anise seed, and in fact many of its derivatives are found in natural and artificial fragrances. The compound is ...

. It can be prepared by

methylation In the chemical sciences, methylation denotes the addition of a methyl group on a substrate, or the substitution of an atom (or group) by a methyl group. Methylation is a form of alkylation, with a methyl group replacing a hydrogen atom. These t ...

thiophenol 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 ...

Reactions

Alkyllithium In organometallic chemistry, organolithium reagents are chemical compounds that contain carbon–lithium (C–Li) bonds. These reagents are important in organic synthesis, and are frequently used to transfer the organic group or the lithium atom ...

reagents deprotonate thioanisole at the

methyl group In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula . In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in many ...

to afford C₆H₅SCH₂Li, a strong

nucleophile In chemistry, a nucleophile is a chemical species that forms bonds by donating an electron pair. All molecules and ions with a free pair of electrons or at least one pi bond can act as nucleophiles. Because nucleophiles donate electrons, they are ...

that can be alkylated to form more complex chains and structures. The resulting

homologated Homologation (Greek ''homologeo'', ὁμολογέω, "to agree") is the granting of approval by an official authority. This may be a court of law, a government department, or an academic or professional body, any of which would normally work f ...

thioether can be manipulated in a variety of ways. Oxidation of sulfur via addition of a single oxygen atom gives methyl phenyl sulfoxide, a reaction useful for

titration Titration (also known as titrimetry and volumetric analysis) is a common laboratory method of quantitative chemical analysis to determine the concentration of an identified analyte (a substance to be analyzed). A reagent, termed the ''titrant'' ...

oxidant An oxidizing agent (also known as an oxidant, oxidizer, electron recipient, or electron acceptor) is a substance in a redox chemical reaction that gains or " accepts"/"receives" an electron from a (called the , , or ). In other words, an oxid ...

s such as

dimethyldioxirane Dimethyldioxirane (DMDO), also referred to as Murray's reagent in reference to Robert W. Murray, is a dioxirane derived from acetone and can be considered as a monomer of acetone peroxide. It is a powerful yet selective oxidizing agent which fin ...

.{{cite journal , title= Spectral and chemical properties of dimethyldioxirane as determined by experiment and ab initio calculations , first1= Waldemar , last1= Adam , first2= Yuk Yee , last2= Chan , first3= Dieter , last3= Cremer , first4= Juergen , last4= Gauss , first5= Dieter , last5= Scheutzow , first6= Michael , last6= Schindler , journal= J. Org. Chem. , year= 1987 , volume= 52 , issue= 13 , pages =2800–2803 , doi= 10.1021/jo00389a029 Successive oxidation then leads to the

sulfone In organic chemistry, a sulfone is a organosulfur compound containing a sulfonyl () functional group attached to two carbon atoms. The central hexavalent sulfur atom is double-bonded to each of two oxygen atoms and has a single bond to each of ...

References

Thioethers Phenyl compounds Foul-smelling chemicals