The gem-dialkyl effect in electron transfer reactions: rapid synthesis of seven-membered rings through an electrochemical annulation.
An electrochemical furan annulation strategy has been developed for the synthesis of seven-membered rings. Key to the success of the annulation is the placement of a gem-dialkyl group in the tether. Voltammetric studies indicate that this effect lowers the oxidation potential by approximately 110 mV.
Sperry
Jeffrey B
JB
Department of Chemistry, Dartmouth College, Hanover, New Hampshire 03755, USA.
Wright
Dennis L
DL
D003500:Cyclization; D003508:Cycloheptanes / Q000138:chemical synthesis* / Q000737:chemistry; D004224:Diterpenes / Q000138:chemical synthesis*; D004563:Electrochemistry; D005663:Furans / Q000737:chemistry*
D003508:Cycloheptanes; D004224:Diterpenes; D005663:Furans; C482765:tricholomalide A