Synthesis and characterization of pentafluorosulfanyl-functionalized fullerenes

Preparation and Characterization of Pentafluoro‐λ6‐sulfanyldifluoromethane and Pentafluoro‐λ6‐sulfanyl‐1,1,2,2‐tetrafluoroethane

“…Other than our 2018 publication in which SF 5 CF 2 I was used to prepare SF 5 ‐functionalized fullerenes, [20] only one reference on SF 5 CF 2 I has appeared in the literature since its initial preparation in 1970 by Knunyants et al [21] . In 2003, Anton , Krespan , and Sievert at DuPont patented the reductions of SF 5 CF 2 I, SF 5 CFICF 3 , and SF 5 CF 2 CF 2 I to the corresponding hydro compounds with molecular hydrogen in the temperature range of 200 to 400 °C; however, none of the examples in their patent included an SF 5 ‐containing compound but instead only examples with iodo‐ and diiodoperfluoroalkanes.…”

“…Reagents were added to glassware either by vacuum‐line transfer or through a syringe through rubber septa. Reagents such as SF 5 CF 2 C(O)OH, [46] SF 5 CF 2 I, [20,21] SF 5 CF 2 CF 2 Br, [47] and SF 5 CF 2 CF 2 I [20,48] were prepared by literature methods, while SF 5 Br, S 2 F 10 , CF 2 =CF 2 (TFE), ICF 2 CF 2 I, CF 3 CF 2 H (HFC‐125) were taken from laboratory stock. For example, TFE was prepared by the thermal decomposition potassium pentafluoropropionate, [49] and 1,2‐diiodotetrafluoroethane was prepared by the addition of iodine to TFE under irradiation by diazo blue (super blue) light (λ max =420 nm), which greatly minimizes the amount of telomerization [50] .…”

Recent Advances in the Synthesis and Medicinal Chemistry of SF5 and SF4Cl Compounds

“…All rights reserved. 71). The conjugates of cytisine and camphecene were synthesized using a different approach, e.g.…”

“…The first SF5-decorated scorpionate [Ph2B(3-(SF5)Pz)2] − was recently described, and some of its copper chemistry was exploited to test the cyclopropanation of styrene with ethyl diazoacetate and CF3CHN2. 70 71 The authors detected an important difference of reactivity between perfluoroalkyl iodides, which typically form (poly)perfluoroalkylfullerenes upon heating, and the SF5CF2CF2I reagent, which produced three types of products, cycloadducts C60(c-C2F4)n, pentafluorosulfanyl products C60(CF2CF2SF5)m, and the mixed derivatives C60(C2F4)n(CF2CF2SF5)m. The product distribution in the reactions with SF5CF2CF2I was found to be highly sensitive to the reaction temperature, however improved selectivity for the bis-adduct 1,7-C60(CF2CF2SF5)2, which was isolated and spectroscopically characterized, was achieved by optimization of the reaction conditions, especially a reaction temperature in the range 140-150 °C. Reactions between C60 and SF5CF2I were also tested, resulting in the formation of a mixture of derivatives with the general formula C60(CF3)n(CF2SF5)m.…”

Functionalization of the C20 fullerene by pyridine and pyrimidine: A theoretical study

“…Because of the electron-deficiency, fullerenes are reactive against dienes and can participate in the Diels-Alder reactions as dienophile [9,10]. Recently, certain experimental and theoretical methods have been developed to functionalize the fullerenes, such as synthesis of C2v(2)-C78Cl6(C5Cl6) [11], synthesis of pentafluorosulfanylfunctionalized fullerenes [12], one-pot substitution of the twenty hydrogen atoms in pentagonal dodecahedrane (C20H20) by OH, F, Cl, and Br [13], functionalization of the C60 fullerene with metformin [14], the Diels-Alder reaction between C60 and acenes [15,16], functionalization of C20 with benzene [17], reaction of C60 with naphthalene [18] and cycloaddition reaction of C20 with pyrene [19]. The Diels-Alder and retro Diels-Alder reactions of the C60 fullerene with 9hydroxy methylanthracene, 9-methoxy methylanthracene and bis(9anthrylmethyl) adipate under solventfree conditions were reported by Wang et al [16].…”