TY - JOUR

T1 - Oxidation of aromatic compounds

T2 - XVI. Radical cations derived from acetylenic compounds with electron-withdrawing groups: Reactions and ESR parameters

AU - Vasil'ev, A. V.

AU - Aristov, S. A.

AU - Fukin, G. K.

AU - Kozhanov, K. A.

AU - Bubnov, M. P.

AU - Cherkasov, V. K.

PY - 2008/6/1

Y1 - 2008/6/1

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=48249091724&partnerID=8YFLogxK

U2 - 10.1134/S1070428008060031

DO - 10.1134/S1070428008060031

M3 - Article

AN - SCOPUS:48249091724

VL - 44

SP - 791

EP - 802

JO - Russian Journal of Organic Chemistry

JF - Russian Journal of Organic Chemistry

SN - 1070-4280

IS - 6

ER -