Abstract
The [3,3]-sigmatropic rearrangement of alkenyl 1-naphthyl sulfides in solutions with various polarities was investigated at 138–190 °C. The reaction proceeds through the formation of 2-alkenyl-1-naphthalene thiols, which subsequently undergo cyclization to compounds of the 2,3-dihydronaphtho[1,2-b]thiophene and naphtho[1,2-b]dihydrothiopyran series. 2-Butenyl 1-naphthyl sulfide, in addition to its passing directly through a [3,3]-sigmatropic rearrangement, to a considerable extent undergoes a prior [1,3]-sigmatropic rearrangement, which ultimately leads to the formation of four cyclic products. The kinetic parameters of the rearrangement of the sulfides were determined. The more negative entropies of activation constitute evidence for the high symmetry of the transition state.
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A. V. Anisimov, V. F. Ionova, V. K. Govorek, V. S. Babaitsev, and E. A. Viktorova, Dokl. Akad. Nauk SSSR, 244, 362 (1979).
H. Kwart and J. L. Schwarts, J. Org. Chem., 39, 1575 (1974).
A. A. Polyakova and R. A. Khmel'nitskii, Mass Spectrometry in Organic Chemistry [in Russian], Khimiya, Leningrad (1972), p. 189.
A. V. Anisimov, R. G. Aukharieva, E. A. Viktorova, and T. A. Danilova, Summaries of Papers Presented at the 9th International Symposium on the Chemistry of Organic Sulfur Compounds [in Russian], Riga (1980), p. 72.
F. Krüger, J. Prakt. Chem., 14, 206 (1876).
A. H. Weinstein and R. M. Pierson, J. Org. Chem., 23, 554 (1958).
T. A. Danilova, T. Abdin, and E. A. Viktorova, Neftekhimiya, 11, 444 (1971).
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Translated from Khimiya Geterotskilicheskikh Soedinenii, No. 5, pp. 611–614, May, 1981.
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Aukharieva, R.G., Danilova, T.A., Anisimov, A.V. et al. [3,3]-Sigmatropic rearrangement of allyl and 2-butenyl 1-naphthyl sulfides. Chem Heterocycl Compd 17, 443–446 (1981). https://doi.org/10.1007/BF00505684
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DOI: https://doi.org/10.1007/BF00505684