An unprecedented skeletal rearrangement of 3-( tert-butylperoxy)indolin-2-one using a tin catalyst has been developed. This rearrangement is highly selective to afford a series of fluorophoric ( Z)-2-arylidene and alkylidene-2 H-benzo[ b][1,4]oxazin-3(4 H)-one derivatives in good to excellent yield. In contrast with Sn(OTf), the reaction of 3-( tert-butylperoxy)indolin-2-one derivatives with FeCl afforded the Hock fragmentation product via C-C bond cleavage.
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| http://dx.doi.org/10.1021/acs.orglett.9b00155 | DOI Listing |
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