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The Decomposition of cis ‐Fused Cyclopenteno‐1,2,4‐Trioxanes induced by Ferrous Salts and some oxophilic reagents
Author(s) -
Jefford Charles W.,
Favarger France,
Vicente Maria Da Graça H.,
Jacquier Yvan
Publication year - 1995
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19950780216
Subject(s) - chemistry , deoxygenation , cyclopentanone , isomerization , reagent , dimer , decomposition , ferrous , thermal decomposition , medicinal chemistry , organic chemistry , catalysis
Two cis ‐fused cyclopenteno‐1,2,4‐trioxanes, 1a and 1b , were subjected to Zn in AcOH or FeCl 2 · 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 ).
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