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.
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.
V Satish
VS
Kumar
Danielle L
DL
Aubele
Paul E
PE
Floreancig
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