Abstract
In contrast to organometallic compounds of the phenyllithium type, cyclooctatetraenyldipotassium on reaction with disulfides and thiocyanato derivatives of the thiophene series in tetrahydrofuran does not give thio ethers but enters into an electron-transfer reaction and is converted to cyclooctatetraene. Thiophene derivatives form the potassium salts of the corresponding thiols. When insufficient amounts of cyclooctatetraenyldipotassium are present, thiocyanatothiophenes are converted to disulfides. It is shown that the latter can be obtained as a result of the reaction of thienyl mercaptides with thiocyanatothiophenes.
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Literature cited
H. Gilman and F. Webb, J. Am. Chem. Soc., 71, 4062 (1949).
S. Gronowitz and R. Hakansson, Arkiv Kemi, 17, 73 (1961).
T. Cantrell and H. Shechter, J. Am. Chem. Soc., 85, 3300 (1963).
Z. V. Todres, V. Sh. Tsveniashvili, S. I. Zhdanov, and D. N. Kursanov, Dokl. Akad. Nauk SSSR, 181, 906 (1968).
K. Kottke, F. Friedrich, and R. Poloudek-Fabini, Arch. Pharm., 300, 583 (1967); Ref. Zh. Khim., 9Zh386 (1968).
Z. V. Todres, Izv. Akad. Nauk SSSR, Ser. Khim., 1749 (1970).
H. Hartough, Thiophene and Its Derivatives, New York, (1952), p. 434.
B. P. Fedorov and F. M. Stoyanovich, Zh. Organ. Khim., 1, 194 (1965).
Ya. L. Gol'dfarb and M. A. Kalik, Khim. Geterotsikl. Soedin., 788 (1968).
E. Reid, Organic Chemistry of Bivalent Sulphur, Vol. 3, New York (1955), p. 356.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 632–636, May, 1973.
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Todres, Z.V., Stoyanovich, F.M., Gol'dfarb, Y.L. et al. Reaction of cyclooctatetraenyldipotassium with disulfides and thiocyanato derivatives of the thiophene series. Chem Heterocycl Compd 9, 583–587 (1973). https://doi.org/10.1007/BF00480568
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DOI: https://doi.org/10.1007/BF00480568