有机化学结构与功能5th答案sg_ch23.pdfVIP

1559T_ch23_409-422 11/09/05 19:28 Page 409 23 Ester Enolates and the Claisen Condensation: Synthesis of -Dicarbonyl Compounds; Acyl Anion Equivalents A large proportion of organic compounds of synthetic and biological importance contain more than one func- tional group. It is obviously necessary to be able to develop methods for the preparation of such substances. You have already learned quite a bit about the aldol condensation and the systems it forms, -hydroxycarbonyl compounds and conjugated enones (Chapter 18). By presenting a related reaction of esters, the Claisen con- densation, this chapter expands the concept of carbonyl condensation reactions. In addition to being a new method for carbon–carbon bond formation, the Claisen condensation gives rise to a class of compounds, - or 1,3-dicarbonyl compounds, that have their own distinct reactivity and utility. The final chapter section presents a more advanced carbon–carbon bond forming method, showing how certain protected forms of carbonyl car- bons may be made nucleophilic and used in displacement reactions. Outline of the Chapter 23-1 -Dicarbonyl Compounds: The Claisen Condensation Construction of the most versatile combination of carbonyl groups. 23-2, 23-3 Synthetic Applications of -Dicarbonyl Compounds 23-4 Alkanoyl (Acyl) Anion Equivalents: Preparation of -Hydroxyketones Reversal of the normal polarity of a functionalized carbon in synthesis. Keys to the Chapter 23-1. -Dicarbonyl Compounds: The Claisen Condensation The Claisen condensation is the main method for