Towards a better understanding of the electrosynthesis of 2,5-dicarboxy-2,5-dihydrofurans: structure, mechanism and influence over stereochemistry.

ABSTRACT: 2,5-Dicarboxy-2,5-dihydrofurans are key constituents of a number of natural products and have roles as intermediates in the formation of other such compounds of interest. Typically, these species are synthesized using toxic Pb(IV) salts. Electrochemical syntheses of 2,5-diacetoxy-2,5-dihydrofuran that do not require the use of lead have been reported, but a general lack of experimental detail has prevented these procedures from being more widely adopted. Moreover, no electrochemical study has yet reported the ratio of cis and trans isomers produced. Herein, we compare the chemical, lead-based route to 2,5-diacetoxy-2,5-dihydrofuran with a fully described electrosynthesis method. In doing so, we have discovered that the cis and trans isomers of this compound were

SUBMITTER: Shipman MA 

PROVIDER: S-EPMC6689595 | biostudies-literature | 2019 Jul

REPOSITORIES: biostudies-literature