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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 26, 1996 - Issue 13
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Original Articles

Pseudoesters and Derivatives XXXV. Reactions of 4-Substituted-5-(Ethylthio)Furan-2(5H)-Ones Anions with Alkylating Agents

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Pages 2573-2586 | Received 02 Feb 1996, Published online: 23 Aug 2006

References

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  • Anions in which the negative charge is spread over three atoms, as shown in the figure
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  • The regiochemical assignments of the new alkylated furanones were based on the spectral data for each compounds. Thus, the 1H-NMR spectra of 3-monoalkylated furanones 4a-c exhibited signals corresponding to the C-5 acetalic proton at 5.8 ppm and lacked olefinic protons. Furthermore, the 13C-NMR spectra of the 5-alkylated furanones 5a-d displayed signals attributed to C-5 quaternary carbon between 91 and 99 ppm and their 1H-NMR spectra lacked acetalic proton
  • The 3,3-dialkylated-2(3H)-furanones 6a-c showed in their IR spectra a band at 1800 cm−1 characteristic of an unconjugated lactonic C=O. Their 1H-NMR spectra lacked signals corresponding to H-3 olefinic proton and H-5 acetalic proton. Their 13C-NMR spectra displayed signals at 180 and 130—142 ppm assigned to C-2 and C-5 quaternary carbons, respectively
  • Fariña , F. , Martín , M. V. and Martinez de Guereñu , A. 1990 . 23 Reunión Bienal de la R. S. E. Q. , Spain : Salamanca .
  • Fariña , F. , Martín , M. V. , Martinez de Guereñu , A. , Ortego , J. L. , Paredes , M. C. and Soto , J. J. 1990 . XIV European Colloquium on Heterocyclic Chemistry , Spain : Toledo .

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