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Diene-transmissive hetero-Diels–Alder reaction of distyryl thioketone

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Merkulova E. A. et al. Diene-transmissive hetero-Diels–Alder reaction of distyryl thioketone // Mendeleev Communications. 2022. Vol. 32. No. 3. pp. 384-385.
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Merkulova E. A., Kolobov A. V., Lyssenko K. A., Nenajdenko V. G. Diene-transmissive hetero-Diels–Alder reaction of distyryl thioketone // Mendeleev Communications. 2022. Vol. 32. No. 3. pp. 384-385.
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TY - JOUR
DO - 10.1016/j.mencom.2022.05.031
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.05.031
TI - Diene-transmissive hetero-Diels–Alder reaction of distyryl thioketone
T2 - Mendeleev Communications
AU - Merkulova, Ekaterina Andreevna
AU - Kolobov, Alexei Vladislavovich
AU - Lyssenko, Konstantin Alexandrovich
AU - Nenajdenko, Valentin Georgievich
PY - 2022
DA - 2022/04/29
PB - Mendeleev Communications
SP - 384-385
IS - 3
VL - 32
ER -
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@article{2022_Merkulova,
author = {Ekaterina Andreevna Merkulova and Alexei Vladislavovich Kolobov and Konstantin Alexandrovich Lyssenko and Valentin Georgievich Nenajdenko},
title = {Diene-transmissive hetero-Diels–Alder reaction of distyryl thioketone},
journal = {Mendeleev Communications},
year = {2022},
volume = {32},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.05.031},
number = {3},
pages = {384--385},
doi = {10.1016/j.mencom.2022.05.031}
}
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Merkulova, Ekaterina Andreevna, et al. “Diene-transmissive hetero-Diels–Alder reaction of distyryl thioketone.” Mendeleev Communications, vol. 32, no. 3, Apr. 2022, pp. 384-385. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.05.031.

Keywords

3,4-dihydro-2H-thiopyrans
diene-transmissive reactions
dienes
dienophiles
enethiones
hetero-Diels–Alder reaction
Lawesson’s reagent
thioketones

Abstract

The reaction distyryl thioketone with donor alkenes (norbornene and styrene) gives adducts of the hetero-Diels–Alder reaction. In the case of maleic acid derivatives, a tandem reaction occurs which leads to polycyclic derivatives of 3,4-dihydro-2H-thiopyran. The stereochemical features of the ongoing transformations were examined.

References

1.
Synthesen in der hydroaromatischen Reihe
Diels O., Alder K.
European Journal of Organic Chemistry, 1928
2.
Fringuelli F., Taticchi A.
2001
5.
Diels_Alder reactions in water
Otto S., Engberts J.B.
Pure and Applied Chemistry, 2000
8.
Development of new methods in modern selective organic synthesis: Preparation of functionalized molecules with atomic precision
Ananikov V.P., Khemchyan L.L., Ivanova Y.V., Bukhtiyarov V.I., Sorokin A.M., Prosvirin I.P., Vatsadze S.Z., Medved'ko A.V., Nuriev V.N., Dilman A.D., Levin V.V., Koptyug I.V., Kovtunov K.V., Zhivonitko V.V., Likholobov V.A., et. al.
Russian Chemical Reviews, 2014
12.
Intermolecular diene-transmissive hetero Diels–Alder reactions of divinyl thioketones
Saito T., Kimura H., Sakamaki K., Karakasa T., Moriyama S.
Chemical Communications, 1996
13.
E. A. Merkulova, A. V. Kolobov and K. L. Ovchinnikov, RF Patent 2670977, 2018.
14.
A convenient synthesise of 3,4-dihydro-2H-thiopyran-2,3-dicarboxylic acid derivatives
Merkulova E.A., Kolobov A.V., Ovchinnikov K.L.
Russian Chemical Bulletin, 2019
15.
Unsaturated carboxylic acids in the one-pot synthesis of novel derivatives of 3,4-dihydro-2H-thiopyran
Merkulova E.А., Kolobov A.V., Ovchinnikov K.L., Khrustalev V.N., Nenajdenko V.G.
Chemistry of Heterocyclic Compounds, 2021
16.
On the Behavior of α,β-Unsaturated Thioaldehydes and Thioketones in the Diels−Alder Reaction
Li G.M., Niu S., Segi M., Tanaka K., Nakajima T., Zingaro R.A., Reibenspies J.H., Hall M.B.
Journal of Organic Chemistry, 2000
17.
Generation and Reactions of Bis(arylmethylene)propanethione
Motoki S., Terauchi Y., Kametani S.
Chemistry Letters, 1988
18.
Lewis acid-promoted hetero Diels–Alder reaction of α,β-unsaturated thioketones
Motoki S., Saito T., Karakasa T., Matsushita T., Furuno E.
Journal of the Chemical Society Perkin Transactions 1, 1992