New gas-phase domino processes leading to benzopyranones and benzofurans
Date
2016Metadata
Show full item recordAbstract
A new domino approach to flavones by gas phase pyrolysis of β,γ-dioxophosphonium ylides containing a 2-methoxyphenyl group is frustrated by unexpected and novel decarbonylation of the intermediate flavon-3-yl radical leading to 2-phenylbenzofuran. Alternative approaches based on dioxolane protection of one carbonyl, or selective elimination in β,β'-dioxo or β-oxo-β'-thioxo ylides were not successful, but pyrolysis of a β-oxo-β'-phenylimino ylide did give the required domino reaction leading to a protected benzopyranone in moderate yield.
Citation
Aitken , R A & Chang , D 2016 , ' New gas-phase domino processes leading to benzopyranones and benzofurans ' , Heterocycles , vol. 93 , no. 1 , pp. 164-184 . https://doi.org/10.3987/COM-15-S(T)14
Publication
Heterocycles
Status
Peer reviewed
ISSN
1881-0942Type
Journal article
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