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http://dx.doi.org/10.13160/ricns.2019.12.3.85

Reactions of 1,1-Dichloro-2,3,4,5-Tetraphenyl-1-Silacyclopentadiene with Magnesium and Lithium  

Hong, Jang-Hwan (Department of Nanopolymer Material Engineering, Pai Chai University)
Publication Information
Journal of Integrative Natural Science / v.12, no.3, 2019 , pp. 85-90 More about this Journal
Abstract
The reaction of 1,1-dichloro-2,3,4,5-tetraphenyl-1-silacyclopentadiene (1) with magnesium-amalgam in THF gave octaphenyl-1,1'-spirobisilole (2), so it was suggested that octaphenyl-1,1'-spirobisilole (2) was produced via the corresponding silolylene species.
Keywords
Metalloles; Silole; Silolylene; Magnesium; ${\alpha}$-Elimination;
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1 Lee VY, Sekiguchi A, Ichinohe M, Fukaya N. Stable aromatic compounds containing heavier group 14 element. J. Organomet. Chem. 2000;611:228-235.   DOI
2 Hissler M, Dyer PW, Reau R. Linear organic ${\pi}$-conjugated systems featuring the heavy group 14 and 15 elements. Coord. Chem. Rev. 2003;244:1-44.   DOI
3 Grutzmacher H. Five-membered aromatic and antianromatic rings with gallium, germanium, and bismuth centers: A short march through the periodic table. Angew. Chem. Int. Ed. Engl. 2005;34:295-298.   DOI
4 Saito M, Yoshiokan Y. The anions and dianions of group 14 metalloles. Coord. Chem. Rev. 2005;249:765-780.   DOI
5 Lee VY, Sekiguchi A. Aromaticity of group 14 organometallics: Experimental aspect. Angew. Chem. Int. Ed. Engl. 2007;46:6596-6620.   DOI
6 Saito M. Challenge to expand the concept of aromaticity to tin- and lead-containing carbocyclic compounds: Synthesis, structures and reactions of dilithiostannoles and dilithioplumbole. Coord. Chem. Rev. 2012;256:627-636.   DOI
7 Joo W-C, Hong J-H, Choi SB, Son H-E, Kim CH. Synthesis and reactivity of 1,1,-disodio-2,3,4,5-tetraphenyl-1-silacyclopentadiene. J. Organomet. Chem. 1990;391:27-36.   DOI
8 Hong JH, Boudjouk P. A stable aromatic species containing silicon. Synthesis and characterization of 1-t-butyl-2,3,4,5-tetraphenyl-1-silacyclopentadienide anion. J. Am. Chem. Soc. 1993;115:5883-5884.   DOI
9 Hong JH, Boudjouk P. Synthesis and characterization of a delocalized germanium-containing dianion: dilithio-2,3,4,5-tetraphenyl-germole. Bull. Soc. Chim. Fr. 1995;132: 495-498.   DOI
10 Hong JH, Boudjouk P. Castellino S. Synthesis and characterization of two aromatic siliconcontaining dianions: The 2,3,4,5-tetraphenylsilole dianion and the 1,1'-disila-2,2',3,3',4,4', 5,5'-octaphenylfulvalene dianion. Organometallics. 1994;13:3387-3389.   DOI
11 West R, Sohn H, Bankwitz U, Calabrese J, Apeloig T, Mueller T. Dilithium derivative of tetraphenylsilole: An ${\eta}^1-{\eta}^5$ dilithium. J. Am. Chem. Soc. 1995;117:11608-11609.   DOI
12 Freeman WP, Tilley TD, Yap GPA, Rheingold AL. Siloyl anions and silole dianions: Structure of $[K([18]crown-6)^+]_2[C4Me4Si^{2-}]$. Angew. Chem. Int. Ed. Engl. 1996;35:882-884.   DOI
13 West R, Sohn H, Powell DR, Muller T, Apeloig Y. Dianion of tetraphenylgermole is aromatic. Angew. Chem., Int. Ed. Engl. 1996;35:1002-1004.   DOI
14 Choi SB, Boudjouk P, Hong JH. Unique Bis-${\eta}^5-{\eta}^1$ bonding in a dianionic germole. Synthesis and structural characterization of the dilithium salt of the 2,3,4,5-tetramethyl germole dianion. Organometallics. 1999;18:2919-2921.   DOI
15 Freeman WP, Tilley TD, Liable-Sands LM, Rheingold AL. Synthesis and study of cyclic ${\pi}$-Systems containing silicon and germanium. The question of aromaticity in cyclopentadienyl analogues. J. Am. Chem. Soc. 1996;118:10457-10468.   DOI
16 B. Goldfuss B, Schleyer PVR, Hampel F. Aromaticity in silole dianions: Structural, energetic, and magnetic aspects. Organometallics. 1996;15:1755-1757.   DOI
17 B. Goldfuss B, Schleyer PVR. Aromaticity in group 14 metalloles: Structural, energetic, and magnetic criteria. Organometallics. 1997;16:1543-1552.   DOI
18 Hong JH, Pan Y, Boudjouk P. A novel lithocenophane derivative of a trisgermole dianion: [Li(thf)(tmeda)] [2,3,4,5-$Et_4$-Ge,Ge-{$Li(2,3,4,5-Et_4C_4Ge)_2$}$C_4Ge$]. Angew. Chem. Int. Ed. Engl. 1996;35:186-188.   DOI
19 Aubouy L, Huby N, Hirsch L, Lee AV D, Gerbier p. Molecular engineering to improve the charge carrier balance in single-layer silole-based OLEDs. New J. Chem.. 2009;33:1290-1300.   DOI
20 Bankwitz U, Sohn H, Powell DR, West R. Synthesis, solid-state structure, and reduction of 1,1-dichloro-2,3,4,5-tetramethylsilole. J. Organomet. Chem. 1995;499:C7-C9.   DOI
21 Sohn H, Powel DR, West R, Hong JH, Joo WC. Dimerization of the Silole Anion $[C4Ph4SiMe]^-$ to a Tricyclic Diallylic Dianion. Organometallics. 1997;16:2770-2772.   DOI
22 Pan Y, Hong JH, Choi SB, Boudjouk P. Surprising reaction of non-nucleophilic bases with 1-hydrosiloles: Addition and not deprotonation. Organometallics. 1997;16:1445-1451.   DOI
23 Hong JH, Boudjouk P. Synthesis and characterization of a novel pentavalent silane: 1-Methyl-1,1-dihydrido-2,3,4,5-tetraphenyl-1-silacyclopentadiene silicate, $[Ph4C4SiMeH2^-]{\cdot}[K^+]$. Organometallics. 1995;14:574-576.   DOI
24 Hong JH. Synthesis and NMR-study of the 2,3,4,5-tetraethylsilole dianion $[SiC_4Et_4]^{2-}{\cdot}2[Li^+]$. Molecules. 2011;16:8033-8040.   DOI
25 Hong JH. Dissociation of the disilatricyclic diallylic dianion $[(C_4Ph_4SiMe)_2]^{-2}$ to the silole anion $[MeSiC_4Ph_4]^-$ by halide ion coordination or halide ion nucleophilic substitution at the silicon atom. Molecules. 2011;16:8451-8462.   DOI
26 Dong Z, Reinhold ZCR, Schmidtmann M, Muller T. Trialkylsilyl-Substituted Silole and Germole Dianions. Organometallics. 2018;37(24):4736-4743.   DOI
27 Tandura SN, Kolesnikov SP, Nosov KS, Lee VY, Egorov MP, Nefedov OM. Electron density distributions in substituted 2, 3, 4, 5-tetraphenyl-1-germacyclopenta-2, 4-dienes studied by NMR spectroscopy. Russian Chemical Bulletin. 1997;46:1859-1861.   DOI
28 Fekete C, Kovacs I, Nyulaszi L, Holczbauer T. Planar lithium silolide: aromaticity, with significant contribution of non-classical resonance structures. Chemical communications (Cambridge, England) 2017;53(80):11064-11067.   DOI
29 Han Z, Xie K, Ma X, Lu X. Synthesis and characterization of a 2, 5-Bis (trimethylsilyl)-substituted Bis (1, 1'-silolide) dianion. Phosphorus, Sulfur, and Silicon and the Related Elements. 2018;193(8):488-492.
30 Gao Y, Zhang J, Hu H, Cui C. Base-Stabilized 1-Silacyclopenta-2,4-dienylidene. Organometallics. 2010; 29:3063-3065.   DOI
31 Wei J, Zhang WX, Xi Z. The aromatic dianion metalloles. Chemical science. 2018;9(3):560-568.   DOI
32 Tamao T, Yamaguchi S, Shiro M. Oligosiloles: first synthesis based on a novel endo-endo mode intramolecular reductive cyclization of diethynylsilanes. Journal of the American Chemical Society. 1994;116(26): 11715-11722.   DOI
33 Lalov AV, Nosov KS, Egorov MP, Nefedov OM. New method of synthesis of 1, 1-bis (trialkylsilyl)-and bis (trialkylgermyl) germacyclopenta-2, 4-dienes. Russian chemical bulletin. 2004;53(10):2334-2335.   DOI
34 Winkler HJ, Gilman H. Preparation and Reactions of sym-Tetraphenyldisilane. The Journal of Organic Chemistry. 1961;26(4):1265-1271.   DOI
35 Zhan X, C. Risko C, Amy F, Chan C, Zhao W, Barlow S, Kahn A, Bredas JL, Marder SR. Electron affinities of 1, 1-diaryl-2, 3, 4, 5-tetraphenylsiloles: directmeasurements and comparison with experimental and theoretical estimates. J. Am. Chem. Soc. 2005;127:9021-9029.   DOI
36 Selin TG, West,R. The reductive coupling of triphenylchlorosilane: Evidence for the triphenylsilyl Grignard reagent, Tetrahedron. 1959;5(1):97-98.   DOI
37 Steudel W, Gilman H. Reactions of Monohaloorganosilanes and Magnesium in Tetrahydrofuran. Journal of the American Chemical Society. 1969;82(23):6129-6132.   DOI
38 Goddard G, Kruger C, Ramadan NA, Ritter A. Silicon Analogues of Grignard Compounds: Synthesis and Structure of Amine?Stabilized Trimethylsilylmagnesium Halides. Angew. Chem. Int. Ed. Engl. 1995;34(9):1030-1032.   DOI
39 Rosch L. Bis (trimethylsilyl) magnesium-The First Organosilyl-magnesium Compound Isolated. Angewante Chemie International Edition in English. 1977;16(4):247-248.   DOI
40 Braye EH, Hubel W, Caplier I. New unsaturated heterocyclic systems. Journal of the American Chemical Society. 1961;83(21):4406-4413.   DOI
41 Sohn,H, Huddleston RR, Powell DR, West R, Oka K, Yonghua X. An electroluminescent polysilole and some dichlorooligosiloles. Journal of the American Chemical Society. 1999;121(12):2935-2936.   DOI