Reactions with N‐Carbonylsulfamoyl Chloride

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Abstract
N‐Carbonylsulfamoyl chloride (NCSA) is an intermediate that can be obtained from cyanogen chloride and sulfur trioxide, and which reacts with many compounds, via electrophilic substitution, much more readily than other isocyanates. Reactions with compounds containing hydroxyl, amino, or carboxyl groups lead to N‐chlorosulfonylurethanes, ‐ureas, and ‐amides, respectively. This group of products also includes the parent substance sulfamoyl chloride (amidosulfonyl chloride). The reaction of N‐carbonylsulfamoyl chloride with olefins provides an easy route, not only to derivatives of β‐amino acids and unsaturated carboxylic acids, but also to many β‐lactams. New, very reactive sulfonylisocyanates of several types can be obtained by further reactions of primary products obtained from N‐carbonylsulfamoyl chloride and by the reaction of N‐carbonylsulfamoyl chloride with olefins in the presence of free‐radical formers. When allowed to react with a number of compounds, NCSA undergoes loss of carbon dioxide to form products containing the grouping = NSO2Cl.

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