The Michael Reactions of Substituted 9,9′-Bifluorenylidenes with 2-Iodo-and 2,7-Diiodofluorene, and Some Other Reactions of Iodofluorenes

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The Michael-addition reaction between 2-iodofluorene and 9,9′-bifluorenylidene gave exclusively the normal addition product. The same reaction of fluorene with 2,2′-diiodo-9,9′-bifluorenylidene, of 2,7-diiodofluorene with 9,9′-bifluorenylidene, and of fluorene with 2,7,2′,7′-tetraiodo-9,9′-bifluorenylidene afforded not only the normal adducts, but also some abnormal compounds. Some new iodo-substituted fluorenes, -9,9′-bifluorenylidenes, -9,9-bifluorenyls, and -1,4-bis(2,2′-biphenylylene)-1,3-butadienes, were synthesized. The hydrogenolyses of 2- or 2,7-di-iodofluorene with lithium aluminum hydride, Raney nickel, and hydriodic acid were performed relatively smoothly to give fluorene. The Grignard and the Ullmann reactions of 2- or 2,7-diiodofluorene gave the usual, expected compounds, accompanied by some unusual products. The cyano-substituted fluorenes were prepared by the reaction of 2- or 2,7-diiodofluorene with potassium cyanide–cupric cyanide in <I>N</I>,<I>N</I>-dimethylformamide.
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