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Paper | Regular issue | Vol 57, No. 10, 2002, pp.1851-1868
Published online, 1st January, 1970
DOI: 10.3987/COM-02-9585
■ About the Factors Which Govern the Ring-Opening of α-Lactams with Primary Amines: II. The Relative Basicity of the Amine

Victor Cesare,* Tony Taldone, and István Lengyel

*Department of Chemistry, St. John’s University, 8000 Utopia Parkway, Jamaica, New York 11439, U.S.A.

Abstract

The ring-opening reaction of four stable α-lactams, 1-(1-adamantyl)-3,3-di-methylaziridinone (1a), 3-(1-adamantyl)-1-triphenylmethyl-aziridinone (1d), 3-tert-butyl-1-triphenylmethylaziridinone (1e), and 1-(1-adamantyl)-3-tert-butylaziridinone (1g) with some substituted benzylamines and other selected primary amines is described. It emerges from the experimental results that the relative basicity of the amine is a decisive factor in determining regioselectivity in the ring-opening.