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8‐Oxabicyclo[5.1.0]octa‐2,4‐dien, reduktive und säurekatalysierte Ringöffnung
Author(s) -
Schiess Peter,
Wisson Markus
Publication year - 1974
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.19740570403
Subject(s) - chemistry , allylic rearrangement , cycloheptatriene , peracetic acid , medicinal chemistry , isomerization , ring (chemistry) , catalytic hydrogenation , hydrolysis , double bond , catalysis , stereochemistry , organic chemistry , hydrogen peroxide
8‐Oxabicyclo[5.1.0]octa‐2,4‐diene ( 1 ) is obtained from cycloheptatriene with commercial 40% peracetic acid. Upon catalytic and LiAlH 4 reduction the allylic CO‐bond in 1 is cleaved. Acid catalised hydrolysis leads to a mixture of all six possible isomeric cycloheptadienediols. With BF 3 in the absence of water isomerization to 3,5‐cycloptadienone is observed.