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Aldehydes and Ketones. Acyl Addition Reactions
Published in Michael B. Smith, A Q&A Approach to Organic Chemistry, 2020
The Schlenk equilibrium describes several organometallic species that comprise the actual structure of a “Grignard reagent” in solution. In its most simple form, the Schlenk equilibrium for a Grignard reagent (RMgX) is: 2RMgX⇄R2Mg+MgX2What is the product of the Grignard reaction between ethylmagnesium bromide and cyclohexanone?
Synthesis of new mesomorphic terphenyl derivatives: the influence of terphenylene and functional fragments on the mesomorphic properties and ligand exchange on quantum dots
Published in Liquid Crystals, 2021
V. S. Bezborodov, A. V. Finko, S. G. Mikhalyonok, Y. I. Derikov, G. А. Shandryuk, N. M. Kuz’menok, A. S. Arol, O. N. Karpov, R. V. Talroze
1-(5-((4ʹʹ-((1s, 4r)-4-butylcyclohexyl)-2ʹ-chloro-[1,1ʹ:4ʹ,1ʹʹ-terphenyl]-4-yl)oxy)pentyl)cyclopropan-1-ol (5). 0.79 g of magnesium turnings were covered with a layer of absolute diethyl ether and 2.7 ml of ethyl bromide in 10 ml of absolute diethyl ether were added with stirring. In a three-necked flask, 5.9 g (0.01 mol) of ethyl 6-((4ʹʹ-((1r, 4s)-4-butylcyclohexyl)-2ʹ-chloro-[1,1ʹ:4ʹ,1ʹʹ-terphenyl]-4-yl)oxy)hexanoate (4). In 200 ml of absolute diethyl ether, 0.72 ml (20 mol%) of tetraisopropyl orthotitanate was added and freshly prepared ethylmagnesium bromide was slowly added dropwise at room temperature and with constant stirring for 0.5 h. After adding all of the ethylmagnesium bromide, the reaction mixture was kept for 2 h at room temperature and 50 ml of 10% sulphuric acid was added to the reaction mixture. The ether layer was separated, the aqueous part was extracted with ether. The ether extracts were combined and dried over MgSO4. The solvent was evaporated and the residue was chromatographed on silica gel. After removing the solvent, the product was crystallised from isopropyl alcohol, m.p. 187оС. Yield 64%. 1H NMR (400 MHz, δ, ppm, CDCl3): 0.42–0.53 (m, 2 H, CH2cyclopropyl), 0.71–0.82 (m, 2 H, CH2cyclopropyl), 0.93 (t, J = 7.0 Hz, 3 H, CH3), 1.03–1.15 (m, 2 H, CH2), 1.22–1.39 (m, 7 H, CH+3× CH2), 1.45–1.67 (m, 6 H, 3× CH2), 1.76–1.99 (m, 8 H, 3× CH2), 2.53 (tt, J = 12.2, 3.2 Hz, 1H, CH), 4.03 (t, J = 6.4 Hz, 2 H, CH2), 6.98 (d, J = 8.7 Hz, 2 H, HAr), 7.31 (d, J = 8.3 Hz, 2 H, HAr), 7.38 (d, J = 8.0 Hz, 1H, HAr), 7.43 (d, J = 8.7 Hz, 2 H, HAr), 7.51 (dd, J = 1.9 Hz, 8.0 Hz, 1H, HAr), 7.54 (d, J = 8.3 Hz, 2 H, HAr), 7.69 (d, J = 1.6 Hz, 1H, HAr).