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The General Synthesis and Trapping of 3-Substituted 1-Chlorocyclopropenes

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https://figshare.com/articles/dataset/The_General_Synthesis_and_Trapping_of_3_Substituted_1_Chlorocyclopropenes/2942050
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Treatment of 1-bromo-2,2-dichloro-3-trimethylsilylcyclopropane with CsF in THF refluxing temperature gave chlorocyclopropenyl cation (1), which reacted with various nucleophiles to generate 3-monosubstituted 1-chlorocyclopropenes. The Diels−Alder reactions of 3-monosubstituted 1-chlorocyclopropenes with 1,3-diphenylisobenzofuran (DPIBF) yielded only the exo-anti adducts in excellent yield. When cation 1 was treated with water and trapped with DPIBF, an aldehyde, 12, was isolated.
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