New gas-phase domino processes leading to benzopyranones and benzofurans

R Alan Aitken, Da Chang

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)


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.
Original languageEnglish
Pages (from-to)164-184
Number of pages21
Issue number1
Early online date6 Oct 2015
Publication statusPublished - 2016


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