Tetrahedron

Synthesis of 6H-dibenzo [b, d] pyran-6-ones via dienone-phenol rearrangements of spiro [2, 5-cyclohexadiene-1, 1′(3′ H)-isobenzofuran]-3′-ones

…, A Kim, R Krishnamurthy, GH Merriman, AM Waltos

Index: Hart, David J.; Kim, Adrienne; Krishnamurthy, Ramanarayanan; Merriman, Gregory H.; Waltos, Anne-Marie Tetrahedron, 1992 , vol. 48, # 38 p. 8179 - 8188

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Citation Number: 17

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 6H-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 ...

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