260262-17-7Relevant academic research and scientific papers
A novel approach to 2-chloro-2-fluorostyrenes
Nenajdenko, Valentine G.,Shastin, Alexey V.,Korotchenko, Vasily N.,Varseev, Georgy N.,Balenkova, Elisabeth S.
, p. 302 - 308 (2007/10/03)
A new general catalytic olefination reaction (COR) of aromatic and heteroaromatic aldehydes and ketones was applied to synthesise 2-chloro-2-fluorostyrenes. The two-stage procedure includes the transformation of carbonyl compounds into hydrazones followed by treatment with CFCl3 mediated by copper catalysis. Trichlorofluoromethane was used as a chlorofluoromethylene transfer reagent. The reaction proceeds stereoselectively and the target alkenes were obtained in high yield. A proposed mechanism for the reaction is discussed. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
Synthesis of fluorinated olefins via the palladium catalyzed cross- coupling reaction of 1-fluorovinyl halides with organoboranes
Chen, Chen,Wilcoxen, Keith,Strack, Nathalie,McCarthy, James R.
, p. 827 - 830 (2007/10/03)
The palladium catalyzed cross-coupling reaction of 1-fluorovinyl halides 1-4 with organoboranes proceeds under Suzuki conditions with retention on configuration to give 1-substituted 1-fluoroolefins 6-8 in good to excellent yields.
PREPARATION AND SYNTHETIC UTILITY OF FLUORINATED PHOSPHONIUM SALTS, BISPHOSPHONIUM SALTS AND PHOSPHORANIUM SALTS
Burton, Donald J.
, p. 339 - 358 (2007/10/02)
The reaction of tertiary phosphines with fluorohalomethanes provides a rapid and high yield synthesis of various types of fluorinated phosphonium salts, bis-phosphonium salts and phosphoranium salts.These salts are useful precursors to fluorine-containing
Proton-Transfer Reactions. 2. Effects of Internal Return on Reactivity Difference between Alkoxide-Promoted Eliminations in tert-Butyl alcohol and Ethyl Alcohol
Koch, H. F.,Tumas, W.,Knoll, R.
, p. 5423 - 5429 (2007/10/02)
Kinetics of alkoxide-promoted dehydrofluorination reactions are reported for the series C6H5CH2CH2F (I), C6H5CH2CHF2 (II), C6H5CH2CF3 (III), and C6H5CH2CF2CF3 (V).Rates and activation parameters 3 (M-1 s-1)(50 deg C), ΔH* (kcal mol-1), and ΔS*, (eu)> are respectively: (a) using potassium tert-butoxide in tert-butyl alcohol, I (1.88 * 10-4, 19.1, -16.8), II (1.18 * 10-3, 20.3, -9.3), III (2.15 * 10-3, 22.1, -2.4), V (3.93 * 10-2, 16.9, -12.7); and (b) using sodium ethoxide in ethanol, I (1.32 * 10-6, 25.6, -6.5), II (5.28 * 10-7, 29.7, 3.0), III (3.45 * 10-7, 32.6, 12.5), V (5.41 * 10-5, 27.7, 7.6).The variation in tert-butoxide:ethoxide ratios of 140 (I), 2200 (II), 6200 (III), and 730 (V) are discussed in terms of a two-step mechanism with varying amounts of internal return for II, III, and V.Differences in reactivity for groups attached to the benzylic carbon (-CF3, -CF2Cl, -CHF2, -CF2CF3) and variation of ΔS* values for these reactions are also discussed in terms of a two-step mechanism.
