Reactions of 1-tert-Butyl-3-phenylaziridinone and α-Bromo-N-tert-butylphenylacetamide with Benzyl-Grignard Reagents

Article abstract of DOI:10.1021/jo00350a014

1-tert-Butyl-3-phenylaziridinone (1) reacts with benzyl halide Grignard reagents (Br and Cl) to give N-tert-butyl-2,3-diphenylpropanamide (4), N-tert-butyl-2-phenylacetamide (3), N-tert-butyl-2-o-tolyl-2-phenylacetamide (5), 1-(tert-butylamino)-1,3-diphenylpropan-2-one (7), N-benzyl-N-tert-butyl-2-phenylacetamide (6), and N-tert-butyl-2-halo-2-phenylacetamide (2, X = Br, Cl).The choice of solvent appears to determine the relative amounts of products 4 and 5.The bromo amide 2 reacts with the Grignard reagent to give 3, 4, 5, 6, and 7 and may be involved to some extentin the reaction of 1 with benzyl-Grignard reagents.The formation of 5 represents anew type of "abnormal" product from a reaction of the benzyl-Grignard reagent; however, this product appears to fit well into the mechanistic pattern established for prior examples.