Conclusions
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1.
1-Phenylpropane-1,2-dione gives a bis-1,3-dithiolane derivative in the reaction with 1,2-ethanedithiol, analogously to glyoxal and phenylglyoxaL Diacetyl and benzil give the corresponding monomercaptals.
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2.
1-Phenylpropane-1,2-dione is reduced in the reaction with 1,2-ethanedithiol, forming 2-ethyl-2-phenyl-1, 3-dithiolane,
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3.
Bis-1,3-dithiolane derivatives of 1-phenylpropane-1, 2-dione, glyoxal, and phenylglyoxal exist in the gauche-form; 2-keto-l,3-dithiolanes from diacetyl and benzil have shielded structures with predominance of the S-conformer.
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Literature cited
T. L. Fridinger and K. R. Henery-Logan, J. Heterocycl. Chem.,8, 469 (1971).
H. Fasbender, Ber.,21, 1473 (1888).
L. F. Fieser, J. Amer. Chem. Soc.,76, 1945 (1954).
W. R. H. Hartley and S. Smiles, J. Chem. Soc., 2263 (1926).
W. Baker and F. B. Field, J. Chem. Soc., 86 (1932).
U. Faass and H. Hilgert, Ber.,87, 1343 (1954).
M. Prostenic and K. Valenovic, J. Organ. Chem.,17, 379 (1952).
T. Posner, Ber.,35, 493 (1902).
L. A. Sternson, D. A. Coviello, and R. S. Egan, J. Amer. Chem. Soc.,93, 6529 (1971).
M. Fuhrer and H. H. Gunthard, Helv. Chim. Acta,45, 2036 (1962).
L. B. Brahde, Acta Chem. Scand.,8, 1145 (1954).
A. N. Vershchagin and O. Exner, Collect, Czechoslov. Chem. Comm.,38, 690 (1973).
O. Exner, V. Jehlicka, and J. Firl, Collect. Czechoslov. Chem. Comm.,37, 466 (1972).
C. Altona and A. P. M. van der Veek, Tetrahedron,24, 4377 (1963).
E. Caspi, T. A. Wittstruck, and D. M. Piatak, J. Organ. Chem.,27, 3183 (1962).
S. Wolf, A. Rauk, L. M. Tel, and I. G. Csizmadia, J. Chem. Soc., B, 136 (1971).
S. Wolf, Accounts Chem. Res.,5, 102 (1972).
S. Wolf, L. M. Tel, J. H. Riang, and I. G. Csizmadia, J. Amer. Chem. Soc.,94, 1361 (1972).
G. Karabatsos, D. Fenoglio, Topics in Stereochemistry, Interscience, John Wiley and Sons, Inc., New York (1970), p. 5.
H. Bock and G. Wagner, Angew Chemie,84, 119 (1972).
Reid and A. Jelinek, J. Organ. Chem.,15, 448 (1950).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2422–2426, November, 1973.
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Arbuzov, B.A., Klimovitskii, E.N., Yuldasheva, L.K. et al. Interaction of certainα-dicarbonyl compounds with ethanedithiol and steric structure of the products formed. Russ Chem Bull 22, 2368–2371 (1973). https://doi.org/10.1007/BF00926373
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DOI: https://doi.org/10.1007/BF00926373