Synthesis and Structures of 1,1′-Dinaphthopyrans

Abstract

The reaction of dinaphthofuran with lithium in anhydrous diethyl ether led to a solution of the corresponding C,O-di­lithiated intermediate which, upon treatment with a range of ketones or aldehydes at -78 °C afforded, after hydrolysis and dehydration, 1,1′-dinaphthopyrans in good yields. The reaction proceeds through reductive ring-opening and cyclization and an intermediate diol was isolated.

Key words

dinaphthofuran - 1,1′-dinaphthopyran - 6H-dinaphtho[b,d]pyran - reductive ring opening

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21

Crystallographic data for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 618573-618578 for compounds 3c, 3d, 3e, 3g, 3h and 4c, respectively. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: [phone] or e-mail: [e-mail]].