Skip to main content
Log in

(2E)-4,4-Dimethoxy-2-butenal in the Synthesis of Conjugated Dienes and Dienals

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

Using (2E)-4,4-dimethoxy-2-butenal as starting compound, methods were developed for synthesis of (2E,4E)- and (2E,4Z)-dimethoxyalkadienes. Deacetalization of the latter gives with high yield the corresponding dienals which are naturally occurring compounds and also synthons for preparation of conjugated dienes as key compounds for building up other natural products.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

REFERENCES

  1. Gree, R., Tourbah, H., and Carrie, R., Tetrahedron Lett., 1986, vol. 27, no. 41, pp. 4983-4986; Meyers, A.I. and Brinkmeyer, R.S., Tetrahedron Lett., 1975, no. 21, pp. 1749-1752.

    Google Scholar 

  2. Khrimyan, A.P., Ovanesyan, A.L., Streinz, L., Svatos, A., Khrimyan, E.P., Makaryan, G.M., and Badanyan, Sh.O., Zh. Bioorg. Khim., 1992, vol. 18, no. 7, pp. 969-978.

    Google Scholar 

  3. Khrimian, A.P., Ovanessian, A.L., Streinz, L., Svatos, A., Romanuk, M., and Badanian, Sh.H., Proc. Conf. on Insecticide Chemistry and Ecology, Tabor, 1990, pp. 137-140.

  4. Ideses, R. and Shani, A., Tetrahedron, 1989, vol. 45, no. 11, pp. 3523-3534.

    Google Scholar 

  5. Naff, F., Decorzant, R., Thommen, W., Willhalm, B., and Ohloff, G., Helv. Chim. Acta, 1975, vol. 58, nos. 109–110, pp. 1016-1037.

    Google Scholar 

  6. Ohloff, G. and Pawlak, M., Helv. Chim. Acta, 1973, vol. 56, no. 3, pp. 1176-1179.

    Google Scholar 

  7. Li Han-Dong, Deng Jan-Neng, Xu Han-Sbeog, Iao Li, and Qu Hai-Sheng, Chin. J. Org. Chem., 1988, vol. 8, no. 2, pp. 167-168.

    Google Scholar 

  8. Kovalev, B.G., Rastegaeva, V.M., Kurts, A.L., and Bundel', Yu.G., Zh. Org. Khim., 1986, vol. 22, no. 9, pp. 1818-1824.

    Google Scholar 

  9. Christmann, K.F., Synthesis, 1969, no. 1, pp. 38-39.

  10. Viola, A. and MacMillan, J.H., J. Am. Chem. Soc., 1970, vol. 92, no. 8, pp. 2404-2410.

    Google Scholar 

  11. Ingham, S., Turner, R.W., and Wallace, T.W., J. Chem. Soc., Chem. Commun., 1985, no. 23, pp. 1664-1666.

  12. Renold, W., Naf-Muller, R., Keller, U., Wilhalm, B., and Ohloff, G., Helv. Chim. Acta, 1974, vol. 57, no. 144, pp. 1301-1308.

    Google Scholar 

  13. Naf, F. and Decorzant, R., Helv. Chim. Acta, 1974, vol. 57, no. 145, pp. 1309-1317.

    Google Scholar 

  14. Goldbach, M., Jakel, E., and Schneider, M.P., J. Chem. Soc., Chem. Commun., 1987, no. 19, pp. 1434-1435.

  15. Tsuboi, S., Masuda, T., and Takedo, A., J. Org. Chem., 1982, vol. 47, no. 23, pp. 4478-4482.

    Google Scholar 

  16. Nakahara, M., Takano, R., Ito, H., Yano, H., Hirase, S., and Harimaya, K., J. Agric. Chem. Soc. Jpn., 1988, vol. 62, no. 2, pp. 157-159; Ref. Zh., Khim., 1989, no. 6E379.

    Google Scholar 

  17. Hara, T., Kubota, E., and Horita, H., J. Agric. Chem. Soc. Jpn., 1987, vol. 61, no. 4, pp. 471-473; Ref. Zh., Khim., 1988, no. 14R436.

    Google Scholar 

  18. Einhorn, J., Beauvais, J., Gallois, M., Descoins, Ch., and Chausse, R., C.R. Acad. Sci., 1984, vol. 299, no. 19, pp. 773-778.

    Google Scholar 

  19. Takeoka, E.R., Flath, R.A., Mon, T.R., Teranishi, R., and Euenert, M., J. Agric. Food Chem., 1990, vol. 38, no. 2, pp. 471-477; Ref. Zh., Khim., 1990, no. 20E16.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Badanyan, S.O., Makaryan, G.M., Ovanesyan, A.L. et al. (2E)-4,4-Dimethoxy-2-butenal in the Synthesis of Conjugated Dienes and Dienals. Russian Journal of Organic Chemistry 37, 633–639 (2001). https://doi.org/10.1023/A:1012479213224

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1012479213224

Keywords

Navigation