1,2,5-Triphenylphosphole reacts with 1-diazoacenaphthen-2-one (1) to give the corresponding strained phosphole ylide (4), which, at 175° in diphenyl ether readily gives 7,10-diphenylfluoranthene (6) while the benzyne-type adduct, 1,4-diphenylnaphthalene, is obtained from (a) 1,2,5-triphenylphosphole and o-bromophenol and (b) 1,2,5-triphenylphosphole oxide and HBr.
J. I. G. Cadogan, R. J. Scott and N. H. Wilson, J. Chem. Soc., Chem. Commun., 1974, 902 DOI: 10.1039/C39740000902
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