Chemistry of Organic Fluorine Compounds 2: A critical Review by Milo%s Hudlický, Attila E. Pavlath

By Milo%s Hudlický, Attila E. Pavlath

Offers entire insurance of the chemistry of natural fluorine compounds. themes contain fluorinating brokers, fluorination techniques, reactions of fluorinated compounds, smooth analytical equipment, and houses and functions of fluorinated compounds. bargains a severe evaluate of the literature and gives over 4,500 references. Updates the 1976 quantity Chemistry of natural Fluorine Compounds.

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Gawley, Synthesis (1976), 777. 1 Main-group chemistry 27 aldol reaction to give the cyclohexenone products 43 may take place in the same pot. g. 52, R CO2 Et). Typical conditions include the use of a base such as KOH in methanol or ethanol, or sodium hydride in an aprotic solvent such as DMSO. 53). 53) + O N Me ii, AcOH, NaOAc H2O O Me 45% Conjugate addition reactions, including the Robinson annulation, which make use of reactive Michael acceptors such as methyl vinyl ketone, can suffer from low yields of the desired adduct.

G. 18) with the ␣,␤-unsaturated carbonyl compound. Although the presence of a protic solvent aids these proton-transfer steps, protic solvents are not a necessity for successful Michael addition reactions. Proton abstraction and conjugate addition can be carried out in the presence of a Lewis acid or by using a base in an aprotic solvent. For example, deprotonation of the dicarbonyl compound 19 with sodium hydride in THF and addition of the Michael 30 E. D. Bergmann, D. Ginsburg and R. Pappo, Org.

Any N-alkylation is reversible and good yields of C-alkylated products are normally obtained. 41). 41) Ar N O Me N Me mesembrine 34 56% R. V. Stevens, Acc. Chem. , 10 (1977), 193. 1 Main-group chemistry 23 The Michael addition is a useful reaction in organic synthesis as it generates a new carbon–carbon single bond under relatively mild and straightforward conditions. 42). 43). There are, however, many examples of the formation of approximately equal mixtures of diastereomers or even high selectivity for the anti stereoisomer.

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