TFA and Lewis acid reactions produced spiro products and conjugated diene-diones, suggesting broad synthetic applications.
A TFA‐catalyzed reaction of fluorene propargylic alcohol with 1,3‐dicarbonyls as nucleophiles, resulting in highly functionalized conjugated diene‐diones appended and propargyl‐substituted 1,3‐dicarbonyl derivatives of fluorenone, has been developed. A plausible mechanism for forming title compounds via allene and propargyl carbocation intermediates has been proposed. On the other hand, the reaction under Lewis acid conditions (BF 3 OEt 2 ) afforded an unusual spirocyclic product, and a plausible mechanism is provided. The scope and synthetic utility of the synthesized products by reduction and base‐promoted cyclization have also been investigated. Spectroscopic data and single‐crystal XRD of the compounds have been utilized to determine the structure of the products.
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Subhashini et al. (2025) studied this question.
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