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Reductive Transformations, 16 [1] Electron Transfer and Regioselectivity in the Alkylation of a Hydrocarbon Mono‐ and Dianion
Author(s) -
Müllen Klaus,
Alexander Jürgen,
Klabunde KayUwe,
Klärner FrankGerrit,
Lund Henning,
Lund Torben
Publication year - 1992
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19921250231
Subject(s) - chemistry , regioselectivity , electrophile , alkylation , electron transfer , annulene , medicinal chemistry , hydrocarbon , photochemistry , stereochemistry , organic chemistry , catalysis
The reductive alkylation of the pyrene isomer 1 affords bridged [14]annulenes ( 2 ) and 2a,3‐dihydro‐2a,3‐dialkyldicyclopenta[ ef,kl ]heptalenes ( 3 ). The involvement of an electron transfer (ET) in this reaction is demonstrated by optically pure electrophiles. Supporting evidence for ET processes is provided by cyclic voltammetric measurement of rate constants for both the ET process and the S N 2 reaction. The choice of the electrophile is relevant not only for the importance of electron transfer, but also for the regioselectivity of the alkylation reaction.