Reactions of the Hydrofluoroborate Salts of Open-Chain Analogues of Reissert Compounds with Some α,β-Ethylenic Esters
1999; Wiley; Volume: 1999; Issue: 1 Linguagem: Inglês
10.1002/(sici)1099-0690(199901)1999
ISSN1434-193X
AutoresSandrine Perrin, Karin Monnier, Bernard Laude, Marek M. Kubicki, Olivier Blacque,
Tópico(s)Fluorine in Organic Chemistry
ResumoThe reaction of the hydrofluoroborate salt of an open-chain analogue of a Reissert compound with some α,β-ethylenic esters does not give a [4 + 2] cycloadduct, as previously described in the case of ethyl acrylate. The reaction starts with a 1,3-dipolar cycloaddition of a münchnone imine 5c, d. The [3 + 2] cycloadducts 13 evolve via a rearrangement–condensation sequence to give a substituted 2-pyridone derivative 18 or 19. The proposed mechanism has been verified by the isolation and structural X-ray analysis of some compounds of the reaction sequence.
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