The Synthesis and Reactions of cis- and trans-Tetrahydrofuran-3, 4-diacetic Acid'

Abstract

cis- and trans-Tetrahydrofuran-3, 4-diacetic acid [6 a and 6 b] were prepared by the ozonization of cis- and trans-8-oxabicyclo[4.3. O]non-3-ene [5 a and 5 b] and subsequent oxidative cleavage of the resulting ozonides with formic acid and hydrogen peroxide mixture. [6 a] was easily converted to anhydride [8 a] and the Dieckmann reaction of the diethyl ester of [6 a] gave cis-2- (ethoxycarbonyl) -7-oxabicyclo[3.3. O]octane-3-one [11 a], however, the same reaction of [6 b] did not proceed. Pyrolysis of [6 a] gave meso-β, β'-bibutyrolactone [9 a] and cis-7- oxabicyclo[3.3.0]-octane-3-one [12], while [6 b] gave dl-β, β'-bibutyrolactone [9 b] only.