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- W2024795638 abstract "While AgI- and PdII-based electrophiles have limited application in cyclisations of allenic amines leading to 7-membered and larger azacycles, these rings may be obtained using iodine as the electrophilic trigger. Iodination of the N-benzyl derivative 5 gives hexahydroazepine 9 either directly or via the isolable allylic iodide 10. The sulfonamide-based allylic iodides 11a–e, produced by direct iodination of allenic sulfonamides 4a–e, cyclise in the presence of NaH, and the product distribution–12vs.13–which depends on the size of rings involved, shows a preference towards formation of the larger ring 13. This chemistry provides a relatively efficient synthesis of 8-, 9-, 10- and 11-membered azacycles 13a–e and 13C and 1H NMR correlations have been applied to assign the (E)/(Z)-alkene geometry of both 13 and related macrocycles 14." @default.
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- W2024795638 date "1994-01-01" @default.
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- W2024795638 title "Allene-based electrophile-mediated cyclisations: efficient synthesis of medium ring azacycles" @default.
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- W2024795638 doi "https://doi.org/10.1039/p19940003549" @default.
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