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Alkali and Alkaline Earth Metal Complexes Ligated by an Ethynyl Substituted Cyclopentadienyl Ligand

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Alkali and Alkaline Earth Metal Complexes Ligated by an Ethynyl Substituted Cyclopentadienyl Ligand inorganics Article Alkali and Alkaline Earth Metal Complexes Ligated by an Ethynyl Substituted Cyclopentadienyl Ligand Tim Seifert and Peter W. Roesky * Institute of Inorganic Chemistry, Karlsruhe Institute of Technology, 76131 Karlsruhe, Germany; [email protected] * Correspondence: [email protected]; Tel.: +49-721-608-46117 Academic Editor: Matthias Westerhausen Received: 30 March 2017; Accepted: 14 April 2017; Published: 20 April 2017 Abstract: Sodium, potassium, and calcium compounds of trimethyl((2,3,4,5- tetramethylcyclopentadien-1-yl)ethynyl)silane (CpMe4(C≡CSiMe3)) were synthesized and characterized by X-ray diffraction and standard analytical methods. The sodium derivative was obtained by deprotonation of CpMe4(C≡CSiMe3)H with Na{N(SiMe3)2} to give a monomeric complex [NaCpMe4(C≡CSiMe3)(THF)3]. In a similar reaction, starting from K{N(SiMe3)2} the corresponding potassium compound [KCpMe4(C≡CSiMe3)(THF)2]n, which forms a polymeric super sandwich structure in the solid state, was obtained. Subsequently, salt metathesis reactions were − conducted in order to investigate the versatility of the CpMe4(C≡CSiMe3) ligand in alkaline earth chemistry. The reaction of [KCpMe4(C≡CSiMe3)(THF)2]n with CaI2 afforded the dimeric complex [CaCpMe4(C≡CSiMe3)I(THF)2]2, in which both CpMe4(C≡CSiMe3)Ca units are bridged by iodide 2 in a µ fashion. In-depth NMR investigation indicates that [CaCpMe4(C≡CSiMe3)I(THF)2]2 is in a Schlenk equilibrium with [{CpMe4(C≡CSiMe3)}2Ca(THF)x] and CaI2(THF)2, as is already known for [CaCp*I(THF)2]. Keywords: calcium; cyclopentadienyl; potassium; sodium 1. Introduction Cyclopentadienyl salts of the alkali metals are probably one of the most versatile reagents in organometallic chemistry. They have been used for the synthesis of countless cyclopentadienyl complexes. Potassium cyclopentadienyl (KCp) was first reported by J. Thiele, who reacted potassium and cyclopentadiene in benzene [1], while the analogous sodium cyclopentadienyl (NaCp) was discovered approximately 50 years later by the groups of E. O. Fischer [2,3] and K. Ziegler [4]. The alkali metal cyclopentadienyls are generally available either by deprotonation of cyclopentadiene with an alkali metal base such as M{N(SiMe3)2}, MH, MOtBu, MOH or the alkali metal itself [5,6]. Some years ago, we showed that sodium and potassium cyclopentadienyl is most conveniently prepared in a one-pot synthesis directly from alkali metals with neat dicyclopentadiene at elevated temperature [7,8]. Especially in the chemistry of electron poor metals, cyclopentadienyl is often 5 used in the form of its permethylated derivative pentamethylcyclopentadienyl η -CpMe5 (Cp*) [8,9], because of the higher solubility of the corresponding metal complexes and the enlarged steric demand of the ligand, which prevents polymerization. Furthermore, other derivatives of cyclopentadienyl are easily accessible and increase the versatility of the cyclopentadienyl ligand [10–12]. For this reason, we became aware of the ligand trimethysilylethynyltetramethylcyclopentadiene CpMe4(C≡CSiMe3)H. − CpMe4(C≡CSiMe3) has been used before in group 8 chemistry. The postmodification of 5 − η -CpMe4(C≡CSiMe3) metal complexes may include access to metal acetylides [13,14], metal alkyne complexes [15,16], Sonogashira couplings [17–19], click reactions [20,21] and cyclizations [22–24]. Inorganics 2017, 5, 28; doi:10.3390/inorganics5020028 www.mdpi.com/journal/inorganics Inorganics 2017, 5, 28 2 of 9 Inorganics 2017, 5, 28 2 of 9 [LiCpMe4(C≡CSiMe3)] has been generated in situ but, to the best of our knowledge, s-block Inorganics[LiCpMe 20174(C, 5,≡ 28CSiMe 3)] has been generated in situ but, to the best of our knowledge, s-block2 of 9 compounds have not been isolated. compounds have not been isolated. [LiCpMe4(C≡CSiMe3)] has been generated in situ but, to the best of our knowledge, s-block 2. Results and Discussion compounds2. Results andhave Discussion not been isolated. CpMeCpMe4(C≡4CSiMe(C≡CSiMe3)H3)H was was prepared prepared in a modified modified procedur proceduree published published by Pudelski by Pudelski et al. et[23] al. [23] 2. Results and Discussion (Scheme(Scheme1). CpMe 1). CpMe4(C≡4(CCSiMe≡CSiMe3)H3)H was was obtainedobtained in in an an overall overall yield yield of 55% of 55% as a aslight a lightyellow yellow oil. oil. CpMe4(C≡CSiMe3)H was prepared in a modified procedure published by Pudelski et al. [23] (Scheme 1). CpMe4(C≡CSiMe3)H was obtained in an overall yield of 55% as a light yellow oil. Scheme 1. Preparation of the ligand CpMe4(C≡CSiMe3)H [23]. Scheme 1. Preparation of the ligand CpMe4(C≡CSiMe3)H [23]. In the first metalation reaction, CpMe4(C≡CSiMe3)H was reacted with Na{N(SiMe3)2} in THF. Scheme 1. Preparation of the ligand CpMe4(C≡CSiMe3)H [23]. InUpon the firstreaction, metalation the reaction,solution CpMe turned4(C≡ CSiMedark 3)Hred, was indicating reacted withthe Na{N(SiMe formation3 )2}of in THF. Upon reaction,[NaCpMe the4(C≡ solutionCSiMe3)(THF) turned3] (1 dark) (Scheme red, indicating2). Single crystals the formation suitable offor[NaCpMe X-ray diffraction4(C≡CSiMe formed3)(THF) in 3] In the first metalation reaction, CpMe4(C≡CSiMe3)H was reacted with Na{N(SiMe3)2} in THF. (1) (Scheme50% yield2). upon Single cooling crystals the concentrated suitable for solution X-ray diffraction to −30 °C. formed in 50% yield upon cooling the Upon reaction, the solution turned dark red, indicating the formation of concentratedThe solutionsodium complex to −30 1◦ C.crystallizes in the monoclinic space group P21/c with one molecule in the [NaCpMe4(C≡CSiMe3)(THF)3] (1) (Scheme 2). Single crystals suitable for X-ray diffraction formed in asymmetric unit (Figure 1). The molecular structure of 1 reveals a monomeric NaCpMe4(C≡CSiMe3) The sodium complex 1 crystallizes in the monoclinic space group P21/c with one molecule in the 50%compound yield upon in thecooling solid the state, concentrated in which CpMe solution4(C≡ toCSiMe −30 °C.3)− coordinates in a η5 fashion to the metal asymmetric unit (Figure1). The molecular structure of 1 reveals a monomeric NaCpMe (C≡CSiMe ) center.The sodiumFurthermore, complex three 1 crystallizes THF molecules in the aremonoclinic attached space to the group sodium P21/ catom. with oneThe moleculecoordination4 in the 3 − 5 compoundasymmetricpolyhedron in unit the thus (Figure solid forms state, 1).a three-leggedThe inmolecular which piano-stool structure CpMe4 (Cconfiguration. of≡ 1CSiMe reveals3 )a Themonomericcoordinates bond distances NaCpMe in between a 4(Cη ≡CSiMefashion the 3) to − 5 thecompound metalcarbon center.atoms in the of solidthe Furthermore, five-membered state, in which three CpMe CpMe THF4(C4(C≡CSiMe≡CSiMe molecules3) ring3) coordinates and are the attached sodium in a ηatom tofashion (Na–C the to sodium =the 2.672– metal atom. Thecenter. coordination2.736 Furthermore,Å) are polyhedronslightly three elongated thusTHF forms comparedmolecules a three-legged to are NaCp attached* [25], piano-stool towhich the issodium configuration.probably atom. caused The The by coordination bondthe steric distances betweenpolyhedrondemand the carbonof thus the forms atomsrather a larger ofthree-legged the TM five-memberedS-ethynyl piano-stool substituent. CpMeconfiguration. 4The(C≡ O–NaCSiMe The–O bond3 )angles ring distances andaverage the between sodiumto 96.2°. the atom (Na–CcarbonCompound = 2.672–2.736 atoms 1of was the Å ) alsofive-membered are characterized slightly elongated CpMe in solution4(C compared≡CSiMe by NMR3) ring to methods. NaCp* and the[ 25The sodium], whichresonances atom is probably (Na–Cof the methyl= caused2.672– by 1 13 the steric2.736groups demandÅ) are splitslightly of into the twoelongated rather signals larger compared(δ( H) TMS-ethynyl = 1.89 to and NaCp 2.02 substituent. *ppm; [25], δ (whichC) = The 10.7 is O–Na–Oprobablyand 11.5 ppm). caused angles The averageby resonance the steric to 96.2 ◦. attributed to the Si(CH3)3 moiety is slightly upfield shifted from 0.22 ppm CpMe4(C≡CSiMe3)H to 0.12 Compounddemand 1ofwas the alsorather characterized larger TMS-ethynyl in solution substituent. by NMR The methods. O–Na–O The angles resonances average of to the 96.2°. methyl Compoundppm (1) in 1 the was 1H alsoNMR characterized spectrum. In inthe solution ATR-IR (ATRby NMR = Attenuated methods. Total The Reflection,resonances IR of = theInfrared) methyl groups are split into two signals (δ(1H) = 1.89 and 2.02 ppm; δ(13C) = 10.7 and 11.5 ppm). The resonance groupsspectrum, are split the Cinto≡C twotriple signals bond of(δ (the1H) ethynyl = 1.89 and moiety 2.02 in ppm; 1 shows δ(13C) a stretching= 10.7 and band 11.5 ppm).at 2118 The cm −resonance1, which attributed to the Si(CH3)3 moiety is slightly4 upfield3 shifted− from1 0.22 ppm CpMe4(C≡CSiMe3)H to attributedis slightly to shifted the Si(CH compared3)3 moiety to CpMe is slightly(C≡CSiMe upfield)H shifted (2131 cmfrom). 0.22 ppm CpMe4(C≡CSiMe3)H to 0.12 1 0.12ppm ppm (1(1) )in in the the 1HH NMR NMR spectrum. spectrum. In Inthe the ATR-IR ATR-IR (ATR (ATR = Attenuated = Attenuated Total Total Reflection, Reflection, IR =IR Infrared) = Infrared ) −1 spectrum,spectrum, the the C≡ CC≡C triple triple bond of of the the ethynyl ethynyl moiety moiety in 1 inshows1 shows a stretching a stretching band at band2118 cm at−1 2118, which cm , −1 whichis slightly is slightly shifted shifted compared compared to CpMe to CpMe4(C≡CSiMe4(C≡3)HCSiMe (21313)H cm (2131−1). cm ). Figure 1. Molecular structure of 1 in the solid state. Hydrogen atoms are omitted for clarity. Selected bond lengths [Å] and angles [°]: Na1–C6 2.691(4), Na1–C7 2.673(4), Na1–C8 2.672(4), Na1–C9 2.717(4), Na1–C10 2.736(4), C4–C5 1.223(6), Na1–O1 2.289(3), Na1–O2 2.321(3), Na1–O3 2.293(3), O1–Na1–O2 96.70(2), O2–Na1–O3 95.75(12), O3–Na1–O1 96.14(12).
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