Electron transfer initiated heterogenerative cascade cyclizations: polyether synthesis under nonacidic conditions.
[reaction: see text] Single-electron oxidation has been employed to initiate heterogenerative cascade cyclization reactions that form polyether compounds under essentially neutral conditions. The reactions proceed through mesolytic benzylic carbon-carbon bond cleavages of homobenzylic ether-derived radical cations followed by intramolecular epoxonium ion formation, leading to further cyclizations. Both oligotetrahydrofuran and tetrahydropyran structures can be prepared by altering substrate topography.
Kumar
V Satish
VS
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.
Aubele
Danielle L
DL
Floreancig
Paul E
PE
D003500:Cyclization; D004583:Electrons; D004852:Epoxy Compounds / Q000737:chemistry; D004987:Ethers / Q000138:chemical synthesis*; D005663:Furans / Q000138:chemical synthesis; D006571:Heterocyclic Compounds / Q000138:chemical synthesis; D010084:Oxidation-Reduction
D004852:Epoxy Compounds; D004987:Ethers; D005663:Furans; D006571:Heterocyclic Compounds; C018674:tetrahydrofuran