Oxidation of aromatic compounds: XVI. Radical cations derived from acetylenic compounds with electron-withdrawing groups: Reactions and ESR parameters |
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| Authors: | A V Vasil’ev S A Aristov G K Fukin K A Kozhanov M P Bubnov V K Cherkasov |
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| Institution: | (1) St. Petersburg State Academy of Forestry Engineering, Institutskii per. 5, St. Petersburg, 194021, Russia;(2) Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, ul. Tropinina 49, Nizhnii Novgorod, 603950, Russia |
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| Abstract: | One-electron oxidation of aryl-substituted acetylenes ArC≡CX where X is an electron-withdrawing group gives different products, depending on the X substituent. Acetylenic substrates with medium-strength electron-withdrawing substituents, X = CO2R, COAr, COR, PO(OEt)2, give rise to tetrasubstituted ethenes X(ArCO)C=C(COAr)X. Compounds with strong electron-withdrawing groups (X = COCF3, COCO2R, CN) are converted into furan derivatives. Probable mechanisms of transformations of ArC≡CX radical cations into the final products are discussed. Radical cations derived from disubstituted acetylenes were characterized by ESR spectroscopy. |
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