Abstract
Allyl 2-benzothienyl sulfide at 20–120 °C undergoes a [3,3]-sigmatropic rearrangement to give 3-allylbenzothiophene-2-thiol. The kinetic parameters of the reaction were studied. Under the experimental conditions the thiol undergoes cyclization to give 2-methyl-2,3-dihydrobenzothieno[2,3-b]thiophene, 2-methyl-benzothieno[2,3-b]thiophene, and benzothieno[2,3-b]dihydrothiopyran. Allyl 3-methyl-2-benzothienyl sulfide does not form a thiol even at 150–190 °C but rather forms only bis(3-methyl-2-benzothienyl) disulfide.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 615–618, May, 1981.
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Anisimov, A.V., Babaitsev, V.S., Grobovenko, S.Y. et al. [3,3]-sigmatropic rearrangement of allyl 2-benzothienyl sulfide. Chem Heterocycl Compd 17, 447–450 (1981). https://doi.org/10.1007/BF00505685
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DOI: https://doi.org/10.1007/BF00505685