The Stereoselective Synthesis and the Nitrogen Interconversion Studies of 2-( tert -butoxymethyl)-1-[NT-(4-methylbenzenesulfonyl) (4-methylphenoxy) imidoyl] aziridine †
Free accessOtherFirst published online April, 2000
The Stereoselective Synthesis and the Nitrogen Interconversion Studies of 2-( tert -butoxymethyl)-1-[NT-(4-methylbenzenesulfonyl) (4-methylphenoxy) imidoyl] aziridine †
One-pot synthesis of the title compound (1) is achieved from tert-butyl allyl ether (2) and the N'(4-methylbenzenesulfonyl) (4-methylphenoxy) imidoyl azide (3) in high yield. The energy barrier of nitrogen interconversion of the title compound (1) was investigated by dynamic NMR. The free energies of activation (AG‡) are 11.11 kcal/mol (Tc = 238 K) and 11.30 kcal/mol (Tc = 242 K) in acetone-d6 and chloroform-d, respectively, and are attributed to nitrogen inversion of aziridine ring nitrogen.
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