Sunday 23 November 2014

ORGANIC SPECTROSCOPY INTERNATIONAL

ORGANIC SPECTROSCOPY INTERNATIONAL:



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Methyl 6-nitro-2-norbornene-5-carboxylate



Methyl (E)-3-nitroacrylate is a reactive dienophile in the Diels-Alder reaction. With cyclopentadiene it gives the corresponding adduct, methyl 6-nitro-2-norbornene-5-carboxylate, in 43% yield in refluxing benzene9 or in quantitive yield in ether at 0°,10 as shown below. The adduct was shown by NMR analysis to consist of an 86 : 14 mixture of endo- : exo-nitro stereoisomers, which could not be separated by crystallization.10



METHYL (E)-3-NITROACRYLATE
[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).


References 
  1. N. F. Blom, D. M. F. Edwards, J. S. Field, and J. P. Michael, J. Chem. Soc. Chem. Commun., 1240 (1980).

Monday 17 November 2014

Drug Patents International

Drug Patents International:



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Making Heterocycles Behave In C-H Activation



 


09246-notw4-catalyst_18751270-690
 
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).

Making Heterocycles Behave In C-H Activation

Organic Chemistry: Reaction overcomes traditional selectivity issues when applied to complex, druglike molecules.
read at
http://cen.acs.org/articles/92/i46/Making-Heterocycles-Behave-CH-Activation.html