In the vapour phase, at temperatures above 400°, bifluorenylidene (1) rearranges fairly cleanly to dibenzo[g,p]-chrysene (2). The reaction is accelerated in the presence of decomposing iodomethane and it is suggested that the mechanism involves a sequence of homoallyl–cyclopropylcarbinyl rearrangements occurring in adduct radicals. The reaction constitutes a simple preparative procedure for (2).
R. W. Alder and G. Whittaker, J. Chem. Soc., Perkin Trans. 2, 1975, 712 DOI: 10.1039/P29750000712
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