New gas-phase domino processes leading to benzopyranones and benzofurans
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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.
Aitken , R A & Chang , D 2016 , ' New gas-phase domino processes leading to benzopyranones and benzofurans ' Heterocycles , vol. 93 , no. 1 , pp. 164-184 . DOI: 10.3987/COM-15-S(T)14
© 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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