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Photochemical reactions. 142 nd communication . Photochemistry of a 6,7‐epoxy‐1,3‐diene of the ionone series
Author(s) -
Mathies Peter,
Frei Bruno,
Jeger Oskar
Publication year - 1985
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.19850680125
Subject(s) - chemistry , ionone , isomerization , photochemistry , ketone , singlet state , diene , ring (chemistry) , enone , medicinal chemistry , stereochemistry , organic chemistry , catalysis , excited state , physics , natural rubber , nuclear physics
On singlet excitation (λ = 254 nm), the epoxydiene ( E )‐ 3 underwent ( E )/( Z )‐isomerization, electrocyclic ring closure of the diene side chain leading to the cyclobutenes 4A + B , and rearrangement to the cyclohexanones 5A + B . Compounds 5A + B were presumably formed in a series of processes including a 1,3‐acyl shift of the homoconjugated ketone 8 , arising from ( Z )‐ 3 by a 1,5‐H‐shift accompanied by cleavage of the C,O‐bond of the oxirane.