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Mechanism of the migration of the substituent in 1,2,3,7a- tetrahydroimidazo[1,2-b]isoxazole derivatives

Russian Chemical Bulletin, ISSN: 1066-5285, Vol: 59, Issue: 9, Page: 1817-1826
2010
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The thermolysis of 1,2,3,7a-tetrahydroimidazo[1,2-b]isoxazole derivatives results in intramolecular rearrangements by two main pathways. One rearrangement affords azomethine ylide derivatives. Another rearrangement leads to the migration of the substituent from position 7a to the nitrogen atom. The rate constants of these reactions were determined. Quantum chemical calculations by the DFT method were carried out. Based on the data for the migration of the substituent, the concerted mechanism was proposed. © 2010 Springer Science+Business Media, Inc.

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