Summary
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1.
When 3,4-bischloromethyl-2-5,dimethylthiophene was treated with water, the condensed system, 1,3,7,9-tetramethyl-4H, 6H, 10H-dithieno[3,4-c,3′,4′-f]oxocin (II) was formed.
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2.
The structure of this product was confirmed by its synthesis from 3,3′-methylbenebis[2,5]dimethylthiophene] by this results of the splitting of the product with thinyl chloride, and by the results of dipole moment measurements.
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3.
No analogs of the compound (II) could be detected among the hydrolysis products of 2,5-di-tert-butyl-3,4-bischloromethylthiophene and of 3,4-bischloromethyl-2,5-dimethylthiophene.
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Literature Cited
T. L. Cairns and B. C. McKusick, J. Org. Chem. 15, 790 (1950).
W. Steinkopf, Ann. 513, 293 (1934).
H. Fischer and P. Halbig, Ann. 447, 123 (1926); H. Fischer and C. Nenitzescu, Ann. 443, 113 (1925).
A. H. Corwin and W. A. Bailey, Jr. and P. Viohl, J. Am. Chem. Soc. 64, 1267 (1942).
Ya. L. Goldfarb and L. M. Smorgonsky, Bull. Acad. Sci. USSR, Div. Chem. Sci. 1936, 66.
Ya. L. Goldfarb and M. S. Kondakova, Bull. Acad. Sci. USSR, Div Chem Schi. 1956, 495 (T.p. 487).
H. Meyer, Analysis and Determination of Organic Compounds (United Sci. Tech. Press, Leningrad, 1937), p. 53.
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Goldfarb, Y.L., Kondakova, M.S. Action of water on 3,4-bischloromethyl-2,5-dimethylthiophene. Russ Chem Bull 5, 1235–1240 (1956). https://doi.org/10.1007/BF01173781
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DOI: https://doi.org/10.1007/BF01173781