2,4-DINITROPHENYLHYDROXYLAMINE: AN EFFICIENT AND MORE GENERAL REAGENT FOR IRON-CATALYZED ALLYLIC AMINATION

Abstract

2,4-Dinitrophenylhydroxylamine (1) is an efficient reagent for the iron-catalyzed regioselective allylic amination of olefins. Moderate to excellent yields of N-DNP-N-allyl amines (2) are obtained resulting from introduction of the N-DNP group at the less substituted vinylic carbon with accompanying double bond transposition. N-alkylation of 2 and subsequent treatment with MeNH₂ affords secondary N-alkyl-N-allyl amines (5) in good overall yield.

ACKNOWLEDGMENTS

We thank Dr. Masood Khan (O. U. Analytical Services X-ray Unit) for determination of the X-ray structure of 2b. We are grateful for support of this project provided by the National Science Foundation.