Synthesis

[4+ 2] Cyclohexane ring formation by a tandem of a free radical alkylation of a non-activated δ-carbon atom and intramolecular carbanion cycloalkylation

G Petrović, Ž Čeković

Index: Petrovic, Goran; Cekovic, Zivorad Synthesis, 2004 , # 10 p. 1671 - 1679

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Abstract

Abstract A [4+ 2] cyclohexane ring formation was achieved by the combination of free radical and ionic reaction sequences. Free radical alkylation of the remote non-activated δ-carbon atom involves addition of δ-carbon radicals, generated by 1, 5-hydrogen transfer in alkoxyl radical intermediates, to the radicophilic olefins, while the polar sequence involves the enolate anions as intermediates which undergo a cycloalkylation reaction. The ...