Reactions of metallated 1-hydroxy-2,2,4,5,5-pentamethyl-2,5-dihydro-1H-imidazole with functionalized nitroxyl radicals derived from 2,5-dihydro-1H-imidazole and 2,5-dihydro-1H-imidazole 3-oxide

The reactions of the dianion generated from 1-hydroxy-2,2,4,5,5-pentamethyl -2,5-dihydro-1H-imidazole under the action of lithium diisopropylamide with nitroxyl radicals derived from 2,5-dihydro-1H-imidazole or 2,5-dihydro-1H- imidazole 3-oxide and containing the ester, aldehydo, cyano, or imino group s afforded biradicals, including those containing the enamino ketone and en amino imine functions. The reactions of this dianion with nitriles derived from 2,5-dihydro-1H-imidazole 3-oxide gave rise to all enamino nitrile, i.e ., electrophilic cyanation formally occurred.