By Chao-Jun Li
An intensive replace of the vintage reference on natural reactions in water released virtually a decade in the past, the 1st variation has served because the consultant for study during this burgeoning box. a result of expense, security, potency, and environmental friendliness of water as a solvent, there are various new purposes in and educational laboratories. greater than 40 percentage of this largely up-to-date moment version covers new reactions. For ease of reference, it really is prepared via useful teams. A middle reference, complete natural Reactions in Aqueous Media, moment variation: * presents the main complete insurance of aqueous organicreactions to be had * Covers the elemental ideas and thought and progresses to functions * comprises alkanes, alkenes, aromatics, electrophilic substitutions, carbonyls, alpha, beta-unsaturated carbonyls, carbon-nitrogen bonds, natural halides, pericyclic reactions, photochemical reactions, click on chemistry, and multi-step syntheses? * presents examples of functions in undefined this can be the top-rated reference for chemists and chemical engineers in or examine, in addition to for college kids in advanced-level classes.
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Extra resources for Comprehensive Organic Reactions in Aqueous Media
30 Labeling experiments with trans-PtDCl(PMe3 )2 show that the hydration involves reductive elimination of a C–H bond. The proposed mechanism involves the attack of hydroxide to the coordinated alkene. 31 The major product is isopropanol. A biopolymer-metal complex, woolsupported palladium-iron complex (wool-Pd-Fe), has been found to be a highly active catalyst for the hydration of some alkenes to the corresponding alcohols. 4 Oxymercuration/Oxymetalation Oxymercuration/demercuration provides a milder alternative for the conventional acid-catalyzed hydration of alkenes.
2 Anti-Dihydroxylation. Hydrogen peroxide in the presence of some oxides, notably tungstic oxide (WO3 ) or selenium dioxide (SeO2 ), reacts with alkenes to give anti-dihydroxlyation products (Eq. 65 The WO3 process is best performed at elevated temperatures (50–70◦ C) and in aqueous solution. Aqueous/organic mixed solvents have also been used successfully to increase the solubility of the alkene in the reaction medium. 68 The lower optical yield was attributed to the presence of a second catalytic cycle that exhibits only low or no enantioselectivity.
Hogan, T. , J. Am. Chem. Soc. 1996, 118, 4574. 28. Gol’dshleger, N. , Tyabin, M. , Shilov, A. , Shteinman, A. , Zh. Fiz. Khim. 1969, 43, 2174 29. Klei, S. , Golden, J. , Tilley, T. , Bergman, R. , J. Am. Chem. Soc. 2002, 124, 2092. 1 Hydrogenation Because of the electron-richness of simple carbon–carbon double bonds, their reduction to C–C single bonds is usually difﬁcult with common electron-rich reducing reagents such as metal hydrides. On the other hand, the use of transition-metal can change the electronic nature of C=C into electron-demanding through coordination with the transition-metals.
Comprehensive Organic Reactions in Aqueous Media by Chao-Jun Li