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The reaction of dinaphthofuran (1), lithium pieces (2.2 equiv), in dry ether led to a solution of the corresponding C,O-dilithiated intermediate 2 which, upon treatment with different ketones or aldehydes (0.8 equiv) at -78 oC, afforded, after hydrolysis and dehydration, highly twisted 1,1′-dinaphthopyrans 3 in good yields. The reaction undergoes reductive ring opening and cyclization, the intermediate diol 4c was isolated. |
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Keywords:Dinaphthofuran, 1,1′-Dinaphthopyran, Reductive ring opening |
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