Detection of Aryl Radicals in Hydrodediazoniations
摘要:
Iodoacetic acid, an effective aryl radical trapping agent, was employed to investigate the reactive intermediates in several hydrodediazoniations. Isolation dan aryl iodide constitutes a positive result in the test for aryl radicals. Equally as important is the lower yield of the reduction product when the trap diverts radicals from their usual reaction path. Hydrodediazoniations performed in MeOH, EtOH, i-PrOH, benzyl alcohol, THF, tetramethylurea, formamide,,and hypophosphorous acid all involve aryl radical intermediates. Ferrocene was found to be an effective initiator in most of these reactions; through its action as an electron donor, it serves to shot-ten reaction times and to improve yields of hydrodediazoniation products. All hydrodediazoniations examined, whether initiated or not, involve radical intermediates.