Indolenine Oxides, VIII. Reaction of 5,7-di-tert-butyl-3,3-dimethyl-3H-indole 1-Oxide with Grignard Reagents. – A New Stable Aminyl Oxide (Nitroxide)

The title compound 1, unsubstituted at C-2, is efficiently converted into its 2-substituted derivatives 4a,b by Grignard addition and lead dioxide oxidation. 4a, when subjected to the same sequence, gives high yields of the aminyl oxide 5a which is also formed in small amounts in the conversion of 1 together with two other minor compounds. The course of the reaction is influenced by the presence of a bulky tert-butyl group at C-7 in 1 and by the solvent used for the Grignard reaction.

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