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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 14, 1984 - Issue 13
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Original Articles

Synthesis of 2-(1-Hydroxyalkyl)acrylonitriles by the Cocatalysis of a Base and an Acid

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Pages 1267-1273 | Published online: 19 Dec 2006

References

  • Takeda , M. and Kaito , M. 1981 . J. Synthetic Org. Chem. Jpn. , 39 : 39
  • Morita , K. , Suzuki , Z. and Hirose , H. 1968 . Bull. Chem. Soc. Jpn. , 41 : 41 see also Miyakoshi, T., Omichi, H., Saito, S., Nippon Kagaku Zasshi, 1979, 748
  • Compared with 5, trimethylaluminium gave a marked decrease (55%) in the yield of the adduct under the same conditions.
  • CH2Cl2 is the solvent of choice, compared to THF, CH3CN, PhH, or t-BuOH
  • When α,β-unsaturated aldehydes (cinnamaldehyde and 2-hexenal) were used instead of the saturated aldehyde under the sarre reaction conditions, only 1,2-adducts were obtained in low yield (19% and 9%, respectively).
  • Baizer , M. M. and Anderson , J. D. 1965 . J. Org. Chem. , 30 : 30
  • McLure , J. D. 1970 . J. Org. Chem. , 35 : 35
  • Hoffmann , H. M. R. and Rabe , J. 1983 . Angew. Chem. Int. Ed. Engl. , 22 : 22 Two interesting reports of the synthesis of 2-(1-hydroxy-alkyl acrylic esters have appeared recently
  • Papageorgion , C. and Benezra , C. 1984 . Tetrahedron Lett. , 25 : 25
  • All nmr spectra were obtained as CDCl3 solution

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