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Sunday, 23 November 2014
is a reactive dienophile in the Diels-Alder reaction. With it gives the corresponding adduct, , in 43% yield in refluxing or in quantitive yield in at 0°, as shown below. The adduct was shown by NMR analysis to consist of an 86 : 14 mixture of endo- : stereoisomers, which could not be separated by crystallization.
[2-Propenoic acid, 3-nitro-, methyl ester (E)-]
1H NMR (60 MHz, CDCl3): δ 3.8 (s, 3H, OCH3), 6.95 (d, J = 14 hz, 1H, =CHNO2-), 7.55 (d, J = 14 Hz, 1H, =CHNO2): IR (CCl4): cm.−1 3100 s, 3000 m, 2950 s, 2880 m (all CH), 1720 s (C=O), 1640 ms (C=C), 1530 s and 1350 s (NO2).
Monday, 17 November 2014
Yu and Dai’s C–H activation method overcomes traditional selectivity limitations, activating the C–H bond next door to a powerful directing group (red bonds).
Organic Chemistry: Reaction overcomes traditional selectivity issues when applied to complex, druglike molecules.