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- W2118065451 abstract "A new series de captodative olefins 3-(2-furoyloxy)-3- buten-2-one and alkyl 2-(2-furoyloxy)-2-propenoates, 3a-3c, has been prepared with the aim of evaluating the effect of a heterocycle in the electron-donating moiety on the reactivity of these compounds in Diels-Alder and conjugate additions. In the former reactions, their behavior has been evaluated by reacting under thermal and catalyzed conditions with cyclopentadiene (9) and cyclohexadiene (12) as the dienes, showing a comparable reactivity, but a lower stereoselectiv- ity, with respect to the reference captodative olefins 1a and 2a. In the case of conjugate additions, the Friedel-Crafts reaction of the highly activated benzene ring of 1,2,4-trimethoxybenzene (7) led to the corresponding adduct 8 only for olefin 3a. Ab initio calculations (HF/6-31G*) of the energies and coefficients of the FMOs were car- ried out to explain the experimental reactivity in both processes. The results suggest that both the electron-withdrawing and the 2-furoy- loxy groups are involved in controlling the reactivity and selectivity" @default.
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- W2118065451 date "2007-12-01" @default.
- W2118065451 modified "2023-10-18" @default.
- W2118065451 title "New Captodative Olefins: 3-(2-Furoyloxy)-3-buten-2-one and Alkyl 2-(2-Furoyloxy)-2-propenoates, and their Reactivity in Addition Reactions" @default.
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- W2118065451 doi "https://doi.org/10.29356/jmcs.v51i4.1282" @default.
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