Reductive Transformations, 16[1] Electron Transfer and Regioselectivity in the Alkylation of a Hydrocarbon Mono- and Dianion
作者： Klaus Müllen , Jürgen Alexander , Kay-Uwe Klabunde , Frank-Gerrit Klärner , Henning Lund
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摘要: The reductive alkylation of the pyrene isomer 1 affords bridged [14]annulenes (2) and 2a,3-dihydro-2a,3-dialkyldicyclopenta[ef,kl]heptalenes (3). involvement an electron transfer (ET) in this reaction is demonstrated by optically pure electrophiles. Supporting evidence for ET processes provided cyclic voltammetric measurement rate constants both process SN2 reaction. choice electrophile relevant not only importance transfer, but also regioselectivity
sci-hub.se 参考文章(54)
W. Huber, W. Irmen, J. Lex, K. Müllen, Reductive transformations : 2. Cis- and trans-1,2-addition of electrophiles to dianionic π-systems Tetrahedron Letters. ,vol. 23, pp. 3889- 3892 ,(1982) , 10.1016/S0040-4039(00)87735-7
L. Nadjo, J.M. Savéant, Linear sweep voltammetry: Kinetic control by charge transfer and/or secondary chemical reactions Journal of Electroanalytical Chemistry and Interfacial Electrochemistry. ,vol. 48, pp. 113- 145 ,(1973) , 10.1016/S0022-0728(73)80300-6
Lennart E. Eberson, Electron transfer reactions in organic chemistry ,(1987)
Klaus Müllen, The Dianions of Pyrene and Pyrene Isomers as (4n)π-Perimeters† Helvetica Chimica Acta. ,vol. 61, pp. 2307- 2317 ,(1978) , 10.1002/HLCA.19780610704
Harold Roy Ward, Ronald G. Lawler, Robert A. Cooper, Chemically induced dynamic nuclear polarization evidence for one-electron transfers during some halogen-metal exchange reactions Journal of the American Chemical Society. ,vol. 91, pp. 746- 748 ,(1969) , 10.1021/JA01031A041
Martin Newcomb, Dennis P. Curran, A Critical Evaluation of Studies Employing Alkenyl Halide 'Mechanistic Probe' as Indicators of Single Electron Transfer Processes. Accounts of Chemical Research. ,vol. 21, pp. 206- 214 ,(1988) , 10.1021/AR00149A005
R. S. Nicholson, Irving. Shain, Theory of Stationary Electrode Polarography. Single Scan and Cyclic Methods Applied to Reversible, Irreversible, and Kinetic Systems. Analytical Chemistry. ,vol. 36, pp. 706- 723 ,(1964) , 10.1021/AC60210A007
C. Schnieders, K. Müllen, W. Huber, The alkali metal reduction of pyrene structural and preparative aspects Tetrahedron. ,vol. 40, pp. 1701- 1711 ,(1984) , 10.1016/S0040-4020(01)91119-6
Donatella Occhialini, Steen U. Pedersen, Henning Lund, C. Rømming, R. Salmén, H. H. Tønnesen, Tadashi Tokii, A Method for Estimating Reduction and Standard Potentials of Unconjugated Alkyl Radicals. Acta Chemica Scandinavica. ,vol. 44, pp. 715- 719 ,(1990) , 10.3891/ACTA.CHEM.SCAND.44-0715
F. G. Bordwell, Craig A. Wilson, Distinguishing between polar and electron-transfer mechanisms for reactions for anions with alkyl halides Journal of the American Chemical Society. ,vol. 109, pp. 5470- 5474 ,(1987) , 10.1021/JA00252A027