THE DECOMPOSITION OF CIS-FUSED CYCLOPENTENO-1,2,4-TRIOXANES INDUCED BY FERROUS SALTS AND SOME OXOPHILIC REAGENTS

Two cis-fused cyclopenteno-1,2,4-trioxanes, 1a and 1b, were subjected to Zn in AcOH or FeCl2 4H(2)O in MeCN. In the first case, the main course was deoxygenation to give cyclopentanone (18) and the 1,4-diphenyl- or 1,4-bis(4-fluorophenyl)cyclopent-3-ene-1,2-diol 10 (Scheme 5). In the second case, isomerization chiefly occurred resulting in the formation of a dimer 9 of the respective 3,5-diaryl-5-hydroxycyclopent-2-enyl 5-hydroxypentanoates 8 (Scheme 3).