Free accessResearch articleFirst published online 2006-2
Synthesis and Dynamic 13 C NMR Study of New System Containing Polarised Carbon–Carbon Double Bonds from Reaction between Cyclohexyl Isocyanide and Ethyl Propiolate in the Presence of N,N′ -Dimethylbarbituric Acid
The adduct produced in the reaction between cyclohexyl isocyanide and ethyl acetylenecarboxylate was trapped by N, N′-dimethylbarbituric acid. Dynamic NMR effects were observed in the NMR spectra of these compounds and were attributed to restricted rotation around the alkyl-nitrogen single bonds and the polarised carbon–carbon double bond.
For chemistry of isocyanides see: Reference 1, WalborskyH.M., PersiasamyM. P., In: PataiS., and RappoportZ. (eds) The Chemistry of Functional Groups, C. Supplement, Wiley, New York, Chap. 20, p 835; Marcasini S., and Torroba T., Org Prep Proced Int., 1993, 25, 141.
16.
HuisgenR., HerbigkK., SieglA., and HuberH., Chem. Ber., 1966, 99, 2526.
17.
SilversteinR.M., BasslerG., and MorrillT. C., Spectrometric Identification of Organic Compounds, 5th edn. John Wiley & Sons, pp. 221, 1991.
18.
ElielE.L., and WilenS. H., Stereochemistry of Organic Compounds, John Wiley & Sons, pp. 571, 1994.
19.
OkiM., Application of Dynamic NMR Spectroscopy to Organic Chemistry, VCH Publishers, 1985.
20.
GuntherH.NMR Spectroscopy, 2nd edn., Chapt 9. Wiley, New York.
21.
AnetF.A. L., and AnetR., In: CottonF.A., and JackmanL. M., (eds) Dynamic Nuclear Magnetic Resonance Spectroscopy.Academic Press: New York, p 543.
