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Synlett 2000; 2000(3): 427
DOI: 10.1055/s-2000-6546
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Chlorosulfonyl Isocyanate

Jean-François Cavalier*
  • *Laboratoire de Chimie Organique, Bât. Lavoisier, Université Catholique de Louvain, Place Louis Pasteur 1, B-1348 Louvain-la-Neuve, Belgium
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Publikationsdatum:
31. Dezember 2000 (online)

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Chlorosulfonyl isocyanate (CSI), is known as the strongest biselectrophile. It is very useful in many synthetic transformations and in the synthesis of various heterocyclic systems.

CSI presents two sites of attack by nucleophiles: at the SO2 group and at the C=O function leading then, to N-sulfonylisocyanate and N-chlorosulfonyl derivatives, respectively, which can be easily functionalized by reaction with water, alcohol or amine. Furthermore, cycloaddition reactions to the C=N double bond of the isocyanate function can also occur.