Palladium Catalysed [3+2] Cycloaddition of Trimethylenemethane to Sulfur Dioxide
13th Paul Walden Symposium on Organic Chemistry: Program and Abstract Book 2023
Emanuels Šūpulnieks, Māris Turks

Trimethylenemethane (TMM) is a known intermediate which can be represented as 4 carbon conjugated structure of diradical or zwitterion. TMM has been shown to react with carbonyl-, iminyl-, cyano- groups and C-C double or triple bonds. Also its reaction with CO2 has been reported previously. Herein, we unveil novel TMM reactivity towards SO2. TMM is generated in situ from easily attainable methylenecyclopropanes 1 through palladium catalysis, then TMM reacts with dissolved SO2 yielding γ-sultines 2. Investigation of γ-sultine 2 reactivity has shown that these products are benchstable, but can regenerate TMM through palladium catalysis, reacting with a nucleophile under milder conditions than described in literature.


Keywords
Palladium, sulfur dioxide, trimethylenemethane, [3+2] cyclisation
Hyperlink
https://walden.osi.lv/wp-content/uploads/2023/09/Abstract_book_Walden_2023.pdf

Šūpulnieks, E., Turks, M. Palladium Catalysed [3+2] Cycloaddition of Trimethylenemethane to Sulfur Dioxide. In: 13th Paul Walden Symposium on Organic Chemistry: Program and Abstract Book, Latvia, Riga, 14-15 September, 2023. Riga: Latvian Institute of Organic Synthesis, 2023, pp.34-34.

Publication language
English (en)
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