Conclusions
-
1.
During the oxidative chlorination of 2-hydroxyethyl octyl sulfide to 2-chloroethyl octyl sulfone with chlorine in water, one of the two oxygen atoms of the sulfone group is incorporated from the reaction media, while the other one originates from the OH group of the oxidizing compound.
-
2.
The sulfur-containing radical does not migrate between the C1 and C2 atoms of the 2-hydroxyethyl group during the oxidative chlorination of 2-hydroxyethyl octyl sulfide and 2-hydroxyethyl octyl sulfoxide.
-
3.
It is assumed that the 2-hydroxyethyl octyl sulfones are formed as a result of an intramolecular rearrangement of a cyclic intermediate alkoxyoxosulfonylchloride where the chlorine does not undergo exchange with the chloride ions of the reaction medium.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
J. S. Jrossert and R. F. Langler, Chem. Commun. 49 (1973).
J. S. Jrossert, W. R. Hardstaff, and R. F. Langler, Chem. Commun., 50 (1973).
U. S. Pat. 3632859 (1972); Ref. Zh. Khim., 19H489 (1972).
S. W. Lee and J. Dougherty, J. Org. Chem.,5, 81 (1940).
U. S. Pat. 3509218 (1970); Ref. Zh. Khim., 6P529 (1971).
S. T. McDowell and C. J. M. Stirling, J. Chem. Soc., B 348 (1967).
German Pat. 887505 (1953); Ref. Zh. Khim., 79274 P (1956).
A. R. Derzhinskii, L. D. Konyushkin, P. V. Vershinin, E. V. Varshaver, M. V. Mokrushin, and E. N. Prilezhaeva, Izv. Akad. Nauk SSSR, Ser. Khim., 937 (1976).
C. R. Johnson and J. J. Rigau, J. Am. Chem. Soc.,91, 5398 (1969).
K. Mislow, T. Simmons, J. T. Melillo, and A. L. Ternay, J. Am. Chem. Soc.86, 1452 (1964).
W. Tagaki, K. Kikukawa, N. Kinieda, and S. Oae, Bull. Chem. Soc., Jpn.,39, 614 (1966).
S. Oae, M. Yokohama, and M. Kise, Bull. Chem. Soc. Jpn.,41, 1221 (1968).
T. Durst and K. C. Tin, Can. J. Chem.,49, 2374 (1971).
T. Durst, K. C. Tin, and M. J. V. Marsil, Can. J. Chem.,51, 1704 (1973).
E. N. Prilezhaeva, T. E. Pivovarova, V. I. Snegotskii, V. H. Syundyukova, V. Z. Sharf, P. V. Saburova, A. L. Petunova, and V. A. Lukin, Chemistry of Organic Sulfur Compounds in Oil and Oil Products [in Russian], Vol. 2, Vsshaya Shkola, (1972), p. 198.
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 850–854, April, 1977.