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- W2098984308 abstract "The radical cyclization reactions of unsaturated sulfonamides were investigated. The photolysis of N-(4-halo-4-pentenyl)sulfonamides (X = I, Br, or Cl) with (diacetoxyiodo)benzene (DIB) and iodine at room temperature afforded exclusively the corresponding piperidines in 73−98% yield via 6-endo radical cyclization. On the other hand, the reactions of N-(5-halo-4-pentenyl)sulfonamides with DIB/I2 led to the only formation of the pyrrolidine products in 84−99% yield via 5-exo radical cyclization. The vinylic halogen substitution not only successfully inhibits the competing ionic iodocyclization process to allow the radical cyclization to proceed smoothly but also shows a remarkable effect in controlling the regioselectivity of cyclization." @default.
- W2098984308 created "2016-06-24" @default.
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- W2098984308 date "2007-03-01" @default.
- W2098984308 modified "2023-10-09" @default.
- W2098984308 title "Control of the Regioselectivity of Sulfonamidyl Radical Cyclization by Vinylic Halogen Substitution" @default.
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- W2098984308 doi "https://doi.org/10.1021/jo0625857" @default.
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