Comparison of tris(dimethylphenylsilyl)methyllithium and tris(trimethylsilyl)methyllithium reactions with carbon disulfide: a new route for the synthesis of some 1,1-bis(benzylthio)- and bis(allylthio)-2,2-bis(dimethylphenylsilyl)ethenes

References

• Pawluc P, Hreczycho G Marciniec B. A new selective approach to 1,1-bis(silyl)- 2-arylethenes and 1,1-bis(silyl)-1,3-butadienes via sequential silylative coupling-heck coupling reactions. J Organomet Chem. 2006;71:8676–8679.
   Web of Science ®Google Scholar
• Inoue A, Kondo J, Shinokubo H, Oshima K. A facile synthesis of 1,1-disilylethenes via Me3MgLi-induced monomethylation of dibromodisilylmethanes. Chem Lett. 2001;30:956–957. doi: 10.1246/cl.2001.956
   Google Scholar
• Safa KD, Ghorbanpour K, Hassanpour A, Tofangdarzadeh S. 1,4-bis[2,2-bis(trimethylsilyl)ethenyl]benzene: regioselective ring opening of its α,β-epoxybis(silane) with some nucleophiles. J Organomet Chem. 2009;694:1907–1911. doi: 10.1016/j.jorganchem.2009.01.030
   Web of Science ®Google Scholar
• Cooke F, Moerck R, Schwindeman J, Magnus P. Silicon in synthesis. 8. Vinyltrimethylsilane, a convenient ethylene equivalent for the synthesis of vinyl arylsulfides, vinyl arylsulfoxides, thiosilylketeneacetals, and fused cyclopentenones. J Organomet Chem. 1980;45:1046–1053.
   Web of Science ®Google Scholar
• Safa KD, Samani SP, Tofangdarzadeh S, Hassanpour A. Study of the reaction of 1,1-bis(trimethylsilyl)-2-phenylethylene with some acyl chlorides in the presence of AlCl3. J Organomet Chem. 2008;693:2004–2008. doi: 10.1016/j.jorganchem.2008.02.032
   Web of Science ®Google Scholar
• Safa KD, Namvari M, Hassanpour A, Tofangdarzadeh S. Synthesis and desilylation of some bis(trimethylsilyl)alkenes and polymers bearing bis(silyl)alkenyl groups. J Organomet Chem. 2009;694:2448–2453. doi: 10.1016/j.jorganchem.2009.03.011
   Web of Science ®Google Scholar
• Safa KD, Hassanpour A, Tofangdarzadeh S. Tris(trimethylsilyl)methane and tris(dimethylphenylsilyl)methane: preparation and comparison of some alkene and cyclopropane derivatives. J Iran Chem Soc. 2009;39:1601–1610.
   Google Scholar
• Safa KD, Hassanpour A, Tofangdarzadeh S. Synthesis of 1,1-bis(silyl)-1-alkene derivatives bearing Si–H functional groups via Peterson protocol. J Organomet Chem. 2008;693:3622–3626. doi: 10.1016/j.jorganchem.2008.08.035
   Web of Science ®Google Scholar
• Safa KD, Hassanpour A, Tofangdarzadeh S, Nasirtabrizi MH. Tris(trimethylsilyl)methane and tris (dimethylphenylsilyl) methane: preparation and comparison of some alkene and cyclopropane derivatives. J Iran Chem Soc. 2008;5:458–463. doi: 10.1007/BF03246003
   Web of Science ®Google Scholar
• Safa KD, Ghorbanpour K. Synthesis of new organosilicon compounds by CS2: mercapto-silyl-thiones. J Organomet Chem. 2013 745–746:214–218. doi: 10.1016/j.jorganchem.2013.07.051
   Web of Science ®Google Scholar
• Safa KD, Ghorbanpour K. New aspects of the chemistry of CS2: synthesis of mercapto-triorganosilyl-thiones by use of tris(trimethylsilyl)methyllithium. J Sulfur Chem. 2014;35(2):170–178. doi: 10.1080/17415993.2013.830726
   Web of Science ®Google Scholar
• Dunn AD, Rudorf WD. Carbon disulphide in organic chemistry. Chichester: Ellis Horwood Limited; 1989. p. 1–389.
   Google Scholar
• Rudorf WD. Reactions of carbon disulfide with C-nucleophiles. Sulfur reports. 1991;11:51–141. doi: 10.1080/01961779108048763
   Web of Science ®Google Scholar
• Seyferth D, Hui RC. Reactions of in-situ generated acyllithium reagents with carbon disulfide and carbonyl sulphide. Tetrahedron Lett. 1984;25:2623–2626. doi: 10.1016/S0040-4039(01)81246-6
   Web of Science ®Google Scholar
• Fleming I, Floyd CD. The reactions of tris(trimethylsilyl)methyl-lithium with some carbon electrophiles. J Chem Soc Perkin Trans (1) 1981:969–976. doi: 10.1039/p19810000969
   Google Scholar
• Wright A, Ling D, Boudjouk P, West R. New anionic rearrangements. XVI. 1,2-Anionic rearrangement from sulfur to carbon in benzylthiotrimethylsilane. J Am Chem Soc. 1972;1972:4784–4785. doi: 10.1021/ja00768a087
   Web of Science ®Google Scholar
• Takeda K, Sumi K, Hagisawa S. Reaction of silylthioketones with lithium diethylphosphite: first observation of Thia–Brook rearrangement. J Organomet Chem. 2000;611:449–454. doi: 10.1016/S0022-328X(00)00482-4
   Web of Science ®Google Scholar
• Kawashima T. New aspects in the chemistry of three-membered ring compounds containing a highly coordinate main group element. Chin J Chem. 2005;23:1267–1269. doi: 10.1002/cjoc.200591267
   Web of Science ®Google Scholar
• Bo LI Zhi-Chao Z, Ying-Ju Z, Kun J, Xiao-Bing LV. Cycloaddition of carbon disulfide with epoxides catalyzed by binary electrophile-nucleophile system. The proceedings of the 3rd international conference on functional molecules. Dalian, China. pp. 119–124.
   Google Scholar
• Durden JA, Stansbury HA, Catlette WH. The preparation of alkene trithiocarbonates. J Am Chem Soc. 1960;82:3082–3084. doi: 10.1021/ja01497a026
   Web of Science ®Google Scholar
• Jesudason MV, Owen LN. Dithiols. Part XXIV. Proof of the epoxide chirality in 2,3-epoxypropyl β-D-glucopyranoside by correlation with (R)-2,3-thiocarbonyldithiopropanol. J Chem Soc Perkin Trans 1. 1974;1974:1443–1446. doi: 10.1039/p19740001443
   Google Scholar
• Grobel T, Seebach D. Erzeugung von und olefinierungmit α-S-, -Se-, -Si- und -Sn-perheterosubstituierten (trimethylsilyl)methyllithium-verbindungen. Chem Ber. 1977;110:852–866. doi: 10.1002/cber.19771100307
   Google Scholar
• Eaborn C, Mansour AI. Reactions at silicon centres bearing the bulky tris(phenyldimethylsilyl)methyl ligand. J Chem Soc Perkin Trans 2. 1985;1985:729–735. doi: 10.1039/p29850000729
   Google Scholar