Arthur G. Schultz

Heteroatom directed photoarylation: synthesis of a tetracyclic morphine structural analogue

The tetracyclic structural analogue (7) of morphine is prepared in high yield by photocyclization-rearrangement of the aryloxyenone (4).

Heteroatom-directed photoarylation: synthesis of indoles and 3-hydroxyindolines

Preparative scale irradiation of 2-anilinoaceto-acetates gives 3-hydroxyindolines, which suffer acid-catalysed dehydration to give indoles.

The photochemistry of cyclohexa-2,5-dien-1-ones. Intramolecular cycloaddition of a furan to an intermediate oxyallyl zwitterion

Photorearrangement of 4-furfuryloxy-2,4,6-trimethylcyclohexa-2,5-dien-1-one (1) gives the bridged furan adduct (4) in 80% yield.

Rearrangement of a 2-aryloxycyclohex-2-enone. A new enolate Claisen rearrangement?

The base-catalysed rearrangement of the 2-aryl-oxycyclohex-2-enone (3) to the enone (4a) is suggested to occur by an enolate-promoted 3,3-sigmatropic rearrangement of the enolate aryl ether (7)