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Paper | Regular issue | Vol 57, No. 4, 2002, pp.677-695
Published online, 1st January, 1970
DOI: 10.3987/COM-02-9453
About the Factors Which Govern the Ring-opening of α-Lactams with Benzylamine I. The Relative Stability of the α-Lactam and the Substituent on Nitrogen

István Lengyel,* Victor Cesare, Sihao Chen, and Tony Taldone

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


Eight α-lactams (aziridinones) of varying stability, one of them previously unreported, were synthesized and reacted with benzylamine. Three of the α-lactams, 1-(1-adamantyl)-3,3-dimethylaziridinone (2j), 3,3-dimethyl-1-triphenylmethylaziridinone (2m), and 3-phenyl-1-triphenylmethyl-aziridinone (2o) gave α-benzylaminoamides (3j, 3m, 3o) as products, indicating C3-N bond cleavage. Four α-lactams, 1,3-di-tert-butylaziridinone (2g), 1-tert-butyl-3-triphenylmethylaziridinone (2i), 1-(1-adamantyl)-3-tert- butylaziridinone (2k), and 1-(1-adamantyl)-3-triphenylmethylaziridinone (2l) yielded N-benzylamides (4g, 4i, 4k, 4l), resulting from C2-N bond cleavage. 3-(1-Adamantyl)-1-triphenylmethylaziridinone (2n) gave a mixture of both types of adduct (3n, 4n). Based on these experimental results, two important factors which govern the ring-opening of α-lactams are the relative stability of the α-lactam and the substituent on nitrogen.