Solvent-dependent transformations of polysubstituted 2-acetyl-2,5-dihydrothiophenes to the corresponding 2-hydroxy- or deacetylated derivatives are described. The treatment of a methanolic solution of the dihydrothiophene substrates with sodium methoxide afforded the deacylated products. Conversely, the treatment with sodium ethoxide in an oxygen saturated ethanolic solution produced 2-hydroxy substituted 2,5-dihydrothiophenes.
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Vladimir G Ilkin
Margarita Likhacheva
Igor V. Trushkov
Beilstein Journal of Organic Chemistry
KU Leuven
Ural Federal University
N.D. Zelinsky Institute of Organic Chemistry
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Ilkin et al. (Wed,) studied this question.
synapsesocial.com/papers/69a75d4dc6e9836116a2718f — DOI: https://doi.org/10.3762/bjoc.22.13
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