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DOI: 10.1055/s-2007-966061
A General Synthetic Route to Dibenzospiropyrans and Dinaphthospiropyrans from Dibenzofuran and Dinaphthofuran
Publication History
Publication Date:
11 May 2007 (online)
Abstract
The reaction of dibenzofuran or dinaphthofuran with lithium in anhydrous diethyl ether led to a solution of the corresponding C,O-dilithiated intermediate which, upon treatment with 1,3,3-trimethylindolin-2-one or different coumarin derivatives at -78 °C, afforded, after hydrolysis, dibenzospiropyrans and dinaphthospiropyrans in good yields. The structures of all new compounds were determined by single crystal X-ray analysis.
Key words
dibenzofuran - dibenzospiropyran - dinaphthofuran - dinaphthospiropyran - reductive ring opening
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References
Crystallographic data for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 638816-638825 for compounds 3-6. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk].