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Methanesulfonyl chloride is a compound containing a sulfonyl chloride used to make methanesulfonates and to generate sulfene.
Additional recommended knowledge
Preparation, manufacture and handling
Methanesulfonyl chloride is highly toxic, moisture sensitive, corrosive, and a lachrymator. It should be stored in dry location, preferably in a dessicator. It is manufactued either via direct synthesis from methane and sulfuryl chloride in a radical reaction (1):
The main use of methanesulfonyl chloride is the formation of methanesulfonates from alcohols and a non-nucleophilic base. Methanesulfonates are used as intermediates in substitution reactions, elimination reactions, reductions, and rearrangement reactions. When treated with a Lewis acid, oxime methanesulfonates will undergo a facile Beckmann rearrangement.
Methanesulfonyl chloride will react with amines to form a methanesulfonamide. Unlike, a methanesulfonate, a methanesulfonamide is a very stable functional group under both acidic and basic conditions. When used as a protecting group, they can be converted back to amines using lithium aluminium hydride or a dissolving metal reduction.
Addition to alkynes
Formation of heterocycles
Upon treatment with a base, such as triethylamine, methanesulfonyl chloride will undergo an alpha-elimination to form sulfene. Sulfene can undergo cycloadditions to form various heterocycles. α-Hydroxyketones react with sulfene to form five-membered sultones.
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Methanesulfonyl_chloride". A list of authors is available in Wikipedia.|