1207196-07-3Relevant academic research and scientific papers
Different reactivity patterns of trimethylsilyl- and phenyl-substituted propargylallenes: Fe2(CO)9- and [Ag]+-promoted cyclizations
Oulie, Pascal,Altes, Lena,Milosevic, Sandra,Bouteille, Romain,Mueller-Bunz, Helge,McGlinchey, Michael J.
experimental part, p. 676 - 686 (2010/05/15)
Thermolytic rearrangement of the diphenyl-propargylallene [3,3-(biphenyl-2,2′-diyl)-1-phenyl-1{9-[(phenylethynyl]-9H-fluorenyl} allene], 9, yields the bis-fluorenyliden-bis-allene 10, which undergoes electrocyclization to form 3,4-di(fluorenyliden)-1,2-diphenylcyclobutene, 12, in which the overlapping fluorenylidenes give rise to C2 symmetry. The propargylallene 9 reacts with iron carbonyls to form 15, in which an (η5-fiuorenyl)Fe(CO)2 moiety is linked both directly and via a bridging =C(Ph)-C(=O)linkage to a cyclobutene ring possessing a phenyl group and a spiro-bonded fluorenyl substituent. The diphenyl-propargylallene 9 and its bis(trimethylsilyl)propargylallene analogue, 2, each react with Co 2(CO)8 to furnish the corresponding alkyne-Co 2(CO)6 complexes 14 and 13, respectively. Treatment of the diphenyl-propargylallene 9 or the mono(trimethylsilyl)propargylallene 25 with silver nitrate in methanol or water effects cyclization of the aliene onto the alkyne to furnish a cyclopentadiene that bears a 9-methoxy- or 9-hydroxy-fluorenyl substituent and is also spiro-bonded to a second fluorenyl moiety. The reaction of 3,3-(biphenyl-2,2′-diyl)-l-bromo-l-phenylallene with Fe2(CO)9 yields the novel bicyclo[3.2.0]heptadienone 21, which possesses two phenyl groups and is also spiro-linked to two fluorenyl fragments. All new compounds were characterized by NMR spectroscopy and X-ray crystallography.
