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
Rights
© 2016 The Japan Institute of Heterocyclic Chemistry. This work has been made available online in accordance with the publisher’s policies. This is the final published version of the work, which was originally published at: https://doi.org/10.3987/COM-15-S(T)14
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