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Sulfonyl halide
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Sulfonyl halide
In chemistry, a sulfonyl halide consists of a sulfonyl (>S(=O)2) group singly bonded to a halogen atom. They have the general formula RSO2X, where X is a halogen. The stability of sulfonyl halides decreases in the order fluorides > chlorides > bromides > iodides, all four types being well known. The sulfonyl chlorides and fluorides are of dominant importance in this series.
Sulfonyl halides have tetrahedral sulfur centres attached to two oxygen atoms, an organic radical, and a halide. In a representative example, methanesulfonyl chloride, the S=O, S−C, and S−Cl bond distances are respectively 142.4, 176.3, and 204.6 pm.
Sulfonic acid chlorides, or sulfonyl chlorides, are a sulfonyl halide with the general formula RSO2Cl.
Arylsulfonyl chlorides are made industrially in a two-step, one-pot reaction from an arene (in this case, benzene) and chlorosulfuric acid:
The intermediate benzenesulfonic acid can be chlorinated with thionyl chloride as well. Benzenesulfonyl chloride, the most important sulfonyl halide, can also be produced by treating sodium benzenesulfonate with phosphorus pentachlorides.
Benzenediazonium chloride reacts with sulfur dioxide and copper(I) chloride to give the sulfonyl chloride:
For alkylsulfonyl chlorides, one synthetic procedure is the Reed reaction:
Sulfonyl chlorides react with water to give the corresponding sulfonic acid:
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Sulfonyl halide
In chemistry, a sulfonyl halide consists of a sulfonyl (>S(=O)2) group singly bonded to a halogen atom. They have the general formula RSO2X, where X is a halogen. The stability of sulfonyl halides decreases in the order fluorides > chlorides > bromides > iodides, all four types being well known. The sulfonyl chlorides and fluorides are of dominant importance in this series.
Sulfonyl halides have tetrahedral sulfur centres attached to two oxygen atoms, an organic radical, and a halide. In a representative example, methanesulfonyl chloride, the S=O, S−C, and S−Cl bond distances are respectively 142.4, 176.3, and 204.6 pm.
Sulfonic acid chlorides, or sulfonyl chlorides, are a sulfonyl halide with the general formula RSO2Cl.
Arylsulfonyl chlorides are made industrially in a two-step, one-pot reaction from an arene (in this case, benzene) and chlorosulfuric acid:
The intermediate benzenesulfonic acid can be chlorinated with thionyl chloride as well. Benzenesulfonyl chloride, the most important sulfonyl halide, can also be produced by treating sodium benzenesulfonate with phosphorus pentachlorides.
Benzenediazonium chloride reacts with sulfur dioxide and copper(I) chloride to give the sulfonyl chloride:
For alkylsulfonyl chlorides, one synthetic procedure is the Reed reaction:
Sulfonyl chlorides react with water to give the corresponding sulfonic acid: