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Farbstoffsensibilisierte Photo‐Oxygenierung von 6,6‐Dimethylfulven . Eine neue 1,2‐Dioxolan‐Umlagerung
Author(s) -
Skorianetz W.,
SchulteWElte K. H.,
Ohloff G.
Publication year - 1971
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.19710540720
Subject(s) - chemistry , epoxide , enol , lactone , photochemistry , stereochemistry , medicinal chemistry , organic chemistry , catalysis
The dye sensitized photo‐oxygenation of 6,6‐dimethylfulvene ( 1 ) in solution at 15° gives enol lactone 2 , along with ketoles 3 and 4. The following mechanism is proposed: initially formed endoperoxide 11 undergoes a 1,2‐dioxolan rearrangement to give allen epoxide 12 , which then isomerizes to cyclopropanone 13. 13 can then cyclise to give 2 and 3 .