Conclusions
-
1.
We have found that, in the process of nucleophilic substitution of vinyls with ionic and nonionic nucleophiles, the reactivity of tris(organosulfonyl)chloroethenes is considerably greater than that for tetrakis(organosulfonyl)ethenes, and, particularly, for 1,2-di(organosulfonyl)-1,2-dichloroethenes.
-
2.
We have discovered multiple reaction pathways for substitution in tris(organo-sulfonyl) chloroethene, combined with the presence in the molecule of two other nucleophiles (RSO2, Cl). We have demonstrated that, under weak nucleophilic conditions, substitution of the RSO2-group is preferred.
Similar content being viewed by others
Literature cited
N. P. Petukhova, N. E. Dontsova, and E. N. Prilezhaeva, Izv. Akad. Nauk SSSR, Ser. Khim., No. 1, 194 (1984).
N. P. Petukhova, N. E. Dontsova, E. N. Prilezhaeva, and V. S. Bogdanova, Izv. Akad. Nauk SSSR, Ser. Khim., No. 3, 611 (1984).
N. E. Dontsova, N. P. Petukhova, E. N. Prilezhaeva, and V. S. Bogdanova, Izv. Akad. Nauk SSSR, Ser. Khim., No. 5, 1104 (1988).
Z. Rappoport, Adv. Phys. Org. Chem.,7, 1 (1969).
C. F. Bernasconi, D. Y. Carre, and A. Kanavarioti, J. Am. Chem. Soc.,103, 4850 (1981).
Z. Rappoport and A. Topol, J. Chem. Soc. Perkin Trans. II, 863 (1975).
E. N. Prilezhaeva, N. E. Dontsova, N. P. Petukhova, et al., Dep. VINITI, No. 1903 1388 (1988).
H. Böhme, Chem. Ber.,69, 1610 (1936).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 649–653, March 1989.
Rights and permissions
About this article
Cite this article
Dontsova, N.E., Sergeeva, V.P., Prilezhaeva, E.N. et al. Polysulfonylethenes. 5. The reactions of tris(organosulfonyl)chloroethenes with amines and thiols. Russ Chem Bull 38, 575–578 (1989). https://doi.org/10.1007/BF00958051
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00958051