Diastereoselective (8+3)‐Cycloadditions of Donor‐Acceptor Cyclopropanes with Tropothione

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 27(6)

Published: Dec. 27, 2023

Abstract Reactions of dimethyl 2‐arylcyclopropane‐1,1‐dicarboxylates, used as representatives D‐A cyclopropanes, with tropothione were carried out in the presence scandium triflate a catalyst, under mild conditions (CH 2 Cl solution, rt). The anticipated (8+3)‐cycloaddition products, cycloheptatriene fused thiopyrans, obtained good to excellent yields. Cycloadditions occurred complete diastereoselectivity and all cases single diastereomers formed. Structures isolated cycloadducts established based on spectroscopic data two they unambiguously confirmed by crystal X‐ray diffraction analysis. In contrast an analogous reported for parent tropone, which was performed Ni(ClO 4 ) , no 1,3‐ H shift leading products possessing CH moiety located within seven‐membered ring observed.

Language: Английский

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Synthesis of Fluorinated and Fluoroalkylated Heterocycles Containing at Least One Sulfur Atom via Cycloaddition Reactions

Materials, Journal Year: 2022, Volume and Issue: 15(20), P. 7244 - 7244

Published: Oct. 17, 2022

Fluorinated heterocycles constitute an important group of organic compounds with a rapidly growing number applications in such areas as medicinal chemistry, agrochemicals production, polymer well chemistry advanced materials. In the latter case, fluorinated thiophenes are considered lead class numerous spectacular applications. On other hand, cycloaddition reactions offer superior methodology for stereo-chemically controlled synthesis diverse ring size and variable heteroatoms. A comprehensive review methods based on applied construction and/or fluoroalkylated S-heterocycles has not yet been published. For this reason, main goal presented was to fill existing gap summarize results published over last six decades. context, [3+2]- [4+2]-cycloadditions (Huisgen reactions, Diels-Alder respectively) special importance. Some questions related discussed mechanisms processes observed electron deficient, substrates (dipolarophiles dienophiles), electron-rich sulfur containing counter partners, fundamental importance development interpretations reaction mechanisms.

Language: Английский

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Some fluorine-containing and sulfur-containing functional new reagents

Synthetic Communications, Journal Year: 2024, Volume and Issue: 54(21), P. 1785 - 1807

Published: Aug. 17, 2024

The research and development of new reagents play a crucial role for organic synthesis. In recent years, numerous with universal applicability have been reported. Recent progress selected fluorine-containing sulfur-containing difluoromethylation, trifluoromethylation thiotrifluoromethylation are summarized. Additionally, some provided, as reagent, Na2S2O4-t-butylhydroperoxide (TBHP) is reagent selective oxidation aromatic alcohols to aldehydes.

Language: Английский

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Five-membered ring systems: With O and S (Se, Te) atoms

Progress in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 259 - 274

Published: Jan. 1, 2024

Language: Английский

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