The Reaction of (h⁵-Cyclopentadienyl)carbonyl(triphenylphosphine)iridium and Bis(pentafluorophenyl)acetylene

Abstract

<jats:title>Abstract</jats:title><jats:p> The reaction between (h<jats:sup>5</jats:sup>-cyclopentadienyl)carbonyl(triphenylphosphine)iridium and bis(pentafluorophenyl)acetylene has been investigated in detail. As in earlier studies involving the analogous cobalt and rhodium complexes, the metallocyclic product 1-(h<jats:sup>5</jats:sup>-cyclopentadienyl)-1-triphenylphosphine-2,3,4,5-tetrakis-pentafluorophenyl)iridole (3) has been obtained, although in very low yield. A variety of highly fluorinated organic products have also been isolated and identified, including hexakis(pentafluorophenyl)-benzene (5), Zraws-1,2-bis(pentafluorophenyl)ethene (6) and 1,2,3,4-tetrakis(pentafluoro-phenyl)naphthalene (4). The latter product has been synthesized by an independent method. Reaction mechanisms to account for the formation of 4 under these conditions are discussed.</jats:p>

Diels–Alder Cycloaddition with CO, CO2, SO2, or N2 Extrusion: A Powerful Tool for Material Chemistry

“…Rausch et al, presented in 1979 the synthesis of tetra(pentafluorophenyl)naphthalene. This compound was obtained via cycloaddition of benzyne (in situ generated from diphenyliodonium-2-carboxylate) to tetrakis(pentafluorophenyl)cyclopentanedione ( Scheme 228 ) [ 288 ].…”

“… Cycloaddition of benzyne to tetraarylcyclopentadienone—synthesis of tetraarylnaphthalene [ 288 ]. Reagents and conditions: Ar = C 6 F 5 ; a = triglyme, 200 °C, 10 min; Y = 27%.…”