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The influence of electronic factors on the rates of N → N′ aroyl migration in N-aroyl-N-(hetero)aryl ethylenediamines has been examined. Electron-withdrawing substituents on the aroyl group were found to weakly accelerate the reaction (in linear correlation with the Hammett σp constants). Much stronger influence came from the nitrogen-bound aromatic group which gave a strong linear correlation with the Hammett σp− constants. For electron-deficient heteroaromatics and nitroaromatics, the migration was nearly instantaneous in basic medium. These findings will significantly impact the planning of mechanistically related transformations of N-(2-aminoethyl) lactams through the hydrated imidazoline ring expansion (HIRE) process.
Original language | English |
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Article number | 152423 |
Number of pages | 4 |
Journal | Tetrahedron Letters |
Volume | 61 |
Issue number | 42 |
DOIs | |
State | Published - 15 Oct 2020 |
ID: 62462942