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Reactions of the Hydrofluoroborate Salts of Open-Chain Analogues of Reissert Compounds with Some α,β-Ethylenic Esters

✍ Scribed by Sandrine Perrin; Karin Monnier; Bernard Laude; Marek Kubicki; Olivier Blacque

Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
245 KB
Volume
1999
Category
Article
ISSN
1434-193X

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✦ Synopsis

The reaction of the hydrofluoroborate salt of an open-chain

The [3 + 2] cycloadducts 13 evolve via a rearrangementcondensation sequence to give a substituted 2-pyridone analogue of a Reissert compound with some α,β-ethylenic esters does not give a [4 + 2] cycloadduct, as previously derivative 18 or 19. The proposed mechanism has been verified by the isolation and structural X-ray analysis of some described in the case of ethyl acrylate. The reaction starts with a 1,3-dipolar cycloaddition of a münchnone imine 5c, d. compounds of the reaction sequence.

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