Abstract
Reactions of 2-(vinyloxy)ethyl isothiocyanate with dicarboxylic acids (malonic, succinic, glutaric, adipic, pimelic, sebacic acids) under nucleophilic conditions (10-15 wt% of Et3N, 55-80°C, 5-50 min) yield quantitatively N,N`-bis[(2-vinyloxy)ethyl]amides.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
REFERENCES
Nedolya, N.A., Tolmachev, S.V., and Zinov'e-va, V.P., Zh. Org. Khim., 2001, vol. 37, no. 8, pp. 1133–1137.
Bogemann, M., Petersen, S., Schultz, O.-E., and Soll, H., Methoden der organischen Chemie (Houben-Weyl), Muller, E., Ed., Stuttgart: Georg Thieme Verlag, 1955, vol. 9, pp. 867–884.
Organic Sulphur Compounds, Kharasch, N., Ed. Pergamon Oxford: Press, 1961, vol. 1, pp. 326–338.
Smith, P.A.S., Open-Chain Nitrogen Compounds, New York: Benjamin, 1965.
Ram, R.N., Ashare, R., and Mukerjee, A.K., Chem. Ind., 1983, no. 14, p. 569.
Drobnica, L., Kristian, P., and Augustin, J., The Chemistry of Cyanates and Their Thio Derivatives, Patai., S., Ed., Chichester: John Wiley & Sons, 1977, part 2, pp. 1003–1221.
Comprehensive Organic Chemistry, Barton, D. and Ollisa, U., Eds., Oxford: Pergamon Press, 1984.
Challis, B.C., and Challis, J.A,, in Comprehensive Organic Chemistry, Sutherland, I.O., Ed., Pergamon Press, Oxford, 1979.
Nedolya, N.A. and Trofimov, B.A., Sulfur Reports, 1994, vol. 15, no. 2, pp. 237–316.
Nedolya, N.A. and Trofimov, B.A., Sulfur Reports, 1994, vol. 15, no. 3, pp. 339–380.
Nedolya, N.A., Brandsma, L., Zinov'eva V.P., Trofimov, B.A., Zh. Org. Khim., 1997, vol. 33, no. 1, pp. 91–96.
Nedolya, N.A., Brandsma, L., Zinov'eva, V.P., and Trofimov, B.A., Zh. Org. Khim., 1998, vol. 34, no. 10, pp. 1559–1564.
Nedolya, N.A., Novel Chemistry Based on Isothiocyanates and Polar Organometallics, PhD. Thesis (Utrecht University, The Netherlands), 1999, 144 p.
Brandsma, L., Nedolya, N.A., Tarasova, O.A., and Trofimov, B.A., Khim. Geterotsikl. Soed., 2000, no. 11, pp. 1443–1463.
Brandsma, L., Tolmachev, S.V., and Nedolya, N.A. Abstracts of Papers, Eurasian Conference on Heterocyclic Compounds, Suzdal, 2000, p. 44.
Nedolya, N.A., Papsheva, N.P., Afonin, A.V., and Trofimov, B.A., Zh. Org. Khim., 1991, vol. 27, no. 10, pp. 2239–2241.
Nedolya, N.A., Papsheva, N.P., Afonin, A.V., Trofimov, B.A., Kukhareva, V.A., and Kashik, T.V., Izv. Akad. Nauk SSSR, Ser. Khim., 1991, no. 10, pp. 2370–2372.
Nedolya, N.A., Papsheva, N.P., Afonin, A.V., Trofimov, B.A., Kukhareva, V.A., and Kashik, T.V., Sulfur Lett., 1992, vol. 14, nos. 2–3, pp. 103–116.
Nedolya, N.A., Gerasimiva, V.V., Papsheva, N.P., and Trofimov, B.A., Sulfur Lett., 1992, vol. 14, nos. 2–3, pp. 117–128.
Nedolya, N.A. and Gerasimova, V.V., Zh. Org. Khim., 1993, vol. 29, no. 2, pp. 265–271.
Nedolya, N.A. and Trofimov, B.A., Zh. Fiz. Khim., 1977, vol. 51, no. 2, pp. 345–348.
Barnes, A.J. and Orville-Thomas, W.J., Vibrational spectroscopy. Modern Trends, Elsevier, 1977.
Durig, J.R. and Gerson, D.J., J. Mol. Struct., 1981, vol. 71, pp. 131–145.
The Chemistry of Amides, Zabicky, J., Ed., New York: John Wiley, 1970.
De Klein, W.J., Spectrochim. Acta, 1971, vol. 27A, no. 1, pp. 93–102.
Trofimov, B.A., Nedolya, N.A., Papsheva, N.P., Gerasimova, V.V., and Voronkov, M.G., Zh. Org. Khim., 1988, vol. 24, no. 8, pp. 1771–1772.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Nedolya, S.A., Tolmachev, S.V., Zinov'yeva, V.P. et al. Vinyl Ethers with Isothiocyanate Group: XIX. Reaction with Dicarboxylic Acids: a Simple Route to N,N'-Bis[(2-vinyloxy)ethyl]amides. Russian Journal of Organic Chemistry 38, 769–774 (2002). https://doi.org/10.1023/A:1020374601246
Issue Date:
DOI: https://doi.org/10.1023/A:1020374601246