Abstract

Chlorosulfonyl isocyanate (CSI) is a sluggish electrophile in reactions with electron-deficient alkenes or with many monofluoroalkenes. The efficiency of these reactions is improved at temperatures between –15 and 25 °C because, at these temperatures, CSI and the alkene are in equilibrium with an intermediate. A unimolecular reaction of the intermediate at a temperature between –15 and 25 °C is more efficient than the bimolecular reaction of the dissociated reagents above room temperature. This finding provides a method for improving the reactions of CSI with unreactive alkenes.

Chlorosulfonyl isocyanate (CSI) is a sluggish electrophile in reactions with electron-deficient alkenes or with many monofluoroalkenes. The efficiency of these reactions is improved at temperatures between –15 and 25 °C because, at these temperatures, CSI and the alkene are in equilibrium with an intermediate. A unimolecular reaction of the intermediate at a temperature between –15 and 25 °C is more efficient than the bimolecular reaction of the dissociated reagents above room temperature. This finding provides a method for improving the reactions of CSI with unreactive alkenes.

中文翻译：

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缓慢的亲电子试剂的改进的合成效用：异氰酸氯磺酰基酯与不活泼和活泼的烯烃的反应

摘要

氯磺酰基异氰酸酯（CSI）在与缺电子的烯烃或许多单氟烯烃反应时是缓慢的亲电子试剂。在–15至25°C之间的温度下，这些反应的效率得以提高，因为在这些温度下，CSI和烯烃与中间体处于平衡状态。中间体在–15至25°C之间的单分子反应比室温以上解离的试剂的双分子反应更有效。该发现提供了改善CSI与非反应性烯烃的反应的方法。

氯磺酰基异氰酸酯（CSI）在与缺电子的烯烃或许多单氟烯烃反应时是缓慢的亲电子试剂。在–15至25°C之间的温度下，这些反应的效率得以提高，因为在这些温度下，CSI和烯烃与中间体处于平衡状态。中间体在–15至25°C之间的单分子反应比室温以上解离的试剂的双分子反应更有效。该发现提供了改善CSI与非反应性烯烃的反应的方法。