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chlorosulfonyl isocyanate : ウィキペディア英語版
chlorosulfonyl isocyanate

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Chlorosulfonyl isocyanate is the chemical compound ClSO2NCO, known as CSI. This compound is a versatile reagent in organic synthesis.
==Preparation, structure, handling==
CSI is prepared by treating cyanogen chloride with sulfur trioxide, the product being distilled directly from the reaction mixture.〔Graf, R. "Chlorosulfonyl Isocyanate" Organic Syntheses, Collected Volume 5, pages 226ff.〕
::SO3 + ClCN → ClSO2NCO
In this transformation, both the carbon and the nitrogen termini of CN are functionalized.
The structure of CSI is represented as ClS(O)2-N=C=O. It consists of two electron-withdrawing components, the chlorosulfonyl group (SO2Cl) and the isocyanate group (-N=C=O). Because of its resulting electrophilicity, the use of CSI in chemical synthesis requires relatively inert solvents such as chlorocarbons, acetonitrile, and ethers.〔Miller, M. J.; Ghosh, M.; Guzzo, P. R.; Vogt, P. F.; Hu, J.; Filzen, G. F.; Geyer, A. G. "Chlorosulfonyl Isocyanate" in "Encyclopedia of Reagents for Organic Synthesis" 2005 John Wiley & Sons: New York.〕

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