Synthesis Of 2-(1-Hydroxyalkyl) Acrylonitriles By The Cocatalysis Of A Base And An Acid

Synthetic Communications

Volumn 14, Issue 13, 1984, Pages 1267-1273

  lmagawa, Takeshi ^a   Uemura, Koichi ^a   Nagai, Zen’ei ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001107683     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397918408076808     Document Type: Article

References (10)

1. Takeda, M., Kaito, M., J. Synthetic Org. Chem. jpn., 1981, 39, 813.
2. Morita, K., Suzuki, Z., Hirose, H., Bull. Chem. Soc. Jpn., 1968, 41, 2815; see also Miyakoshi, T., Omichi, H., Saito, S., Nippon Kagaku Zasshi, 1979, 748.
3. Compared with 5, trimethylaluminium gave a marked decrease (55%) in the yield of the adduct under the same conditions.
4. CH2Cl2is the solvent of choice, compared to THF, CH3CN, PhH, or t-BuOH
5. When ±, ±-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).
6. Baizer, M. M., Anderson, J. D., J. Org. Chem., 1965, 30, 1357.
7. McLure, J. D., J. Org. Chem., 1970, 35, 3045.
8. Two interesting reports of the synthesis of 2-(1-hydroxy-alkyl) acrylic esters have appeared recently; (a) Hoffmann, H. M. R., Rabe, J., Angew. Chem. Int. Ed. Engl., 1983, 22, 795;
9. Papageorgion, C., Benezra, C., Tetrahedron Lett., 1984, 25, 1303.
10. All nmr spectra were obtained as CDCl3solution.