Abstract
A series of spiro[2,5-cyclohexadiene-1,1′(3′ H)-isobenzofuran]-3′-ones were prepared from metalled benzamides and 4,4-dimethoxycyclohexadienone. Rearrangement of these spirodienones under a variety of conditions gave substituted 6 H-dibenzo[ b,d]pyran-6-ones. Rearrangements in aqueous sulfuric acid gave products of formal O-migration while rearrangements in trifluoroacetic anhydride-trifluoroacetic acid-sulfuric acid usually gave C-mitration products.
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