0000000000114801
AUTHOR
Sandrine Perrin
ChemInform Abstract: Reactions of the Hydrofluoroborate Salts of Open-Chain Analogues of Reissert Compounds with Some α,β-Ethylenic Esters.
The 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 munchnone 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.
Reaction of an open-chain analogue of Reissert compound hydrofluoroborate salt with ethyl acrylate. A reinvestigation
Abstract The reaction of an open-chain analogue of Reissert compound hydrofluoroborate salt with ethyl acrylate does not give a [4+2] cycloadduct as previously described, but a [3+2] cycloadduct which evolves to a 2-pyridone 15.
Reactions of the hydrofluoroborate salts of open-chain analogues of Reissert compounds with some α,β-ethylenic esters
The 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 munchnone 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.