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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.
Halogens give initially 2-halo derivatives followed by 2,5-dihalothiophenes; perhalogenation is easily accomplished to give C 4 X 4 S (X = Cl, Br, I). [20] Thiophene brominates 10 7 times faster than does benzene. Acetylation occurs readily to give 2-acetylthiophene, precursor to thiophene-2-carboxylic acid and thiophene-2-acetic acid. [9]
In chemistry, a sulfonyl halide consists of a sulfonyl (>S(=O) 2) group singly bonded to a halogen atom. They have the general formula RSO 2 X , where X is a halogen. The stability of sulfonyl halides decreases in the order fluorides > chlorides > bromides > iodides , all four types being well known.
ClCH 2 CO 2 H + Na 2 S 2 O 3 → Na[O 3 S 2 CH 2 CO 2 H] + NaCl Na[O 3 S 2 CH 2 CO 2 H] + H 2 O → HSCH 2 CO 2 H + NaHSO 4. Organolithium compounds and Grignard reagents react with sulfur to give the thiolates, which are readily hydrolyzed: [27] RLi + S → RSLi RSLi + HCl → RSH + LiCl. Phenols can be converted to the thiophenols via ...
Sulfuryl chloride is used as a source of Cl 2. Because it is a pourable liquid, it is considered more convenient than Cl 2 to dispense. Sulfuryl chloride is used in the conversion of C−H to C−Cl adjacent to activating substituents such as carbonyls and sulfoxides: [5] [6] RC(O)CH 2 R' + SO 2 Cl 2 → RC(O)CHClR' + HCl + SO 2
Sulfonyl groups can be written as having the general formula R−S(=O) 2 −R′, where there are two double bonds between the sulfur and oxygen. [1]: 53 [2] Sulfonyl groups can be reduced to the sulfide with diisobutylaluminium hydride (DIBALH). Lithium aluminium hydride (LiAlH 4) reduces some but not all sulfones to sulfides. [1]: 1851
Thereafter a chlorine atom attacks the hydrocarbon chain, freeing hydrogen to form hydrogen chloride and an alkyl free radical. The resulting radical then captures SO 2. The resulting sulfonyl radical attacks another chlorine molecule to produce the desired sulfonyl chloride and a new chlorine atom, which continues the reaction chain. Chain ...
The sulfonyl functional group (RS(O) 2 R') has become an important electron-withdrawing group for modern organic chemistry. α-Sulfonyl carbanions may be used as nucleophiles in alkylation reactions, Michael-type additions, and other processes. [3] After having served their synthetic purpose, sulfonyl groups are often removed.