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By Francis A. Carey

The two-part, 5th version of complex natural Chemistry has been considerably revised and reorganized for higher readability. the cloth has been up-to-date to mirror advances within the box because the prior variation, specifically in computational chemistry. half B describes the main basic and helpful artificial reactions, geared up at the foundation of response kind. it could possibly stand-alone; jointly, with half A: constitution and Mechanisms, the 2 volumes supply a complete origin for the examine in natural chemistry. spouse web content supply electronic types for college kids and workout strategies for instructors.

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Advanced Organic Chemistry: Part B: Reactions and Synthesis

The two-part, 5th variation of complicated natural Chemistry has been considerably revised and reorganized for better readability. the cloth has been up-to-date to mirror advances within the box because the prior version, in particular in computational chemistry. half B describes the main normal and invaluable artificial reactions, geared up at the foundation of response kind.

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Chem. 22,346 (1957). W. Wayne and H. Adkins,!. Am. Chem. Soc. 62, 3401 (1940). f. D. J. Baisted and J. S. Whitehurst,!. Chern. , 4089 (1961). g. G. A. Hill and G. Bramann, Org. Synth. I, 81 (1941). h. S. C. Bunce, H. J. Dorsman, and F. D. Popp,!. Chem. , 303 (1963). i. A. M. Islam and M. T. Zemaity, J. Am. Chem. Soc. 79, 6023 (1957). j. D. Meuche, H. Strauss, and E. Heilbronner, Helv. Chim. Acta 41,2220 (1958). k. A. I. Meyers and N. Naurenko, !. Org. Chem. 38, 175 (1973). 1. R. Noyori, K. Yokoyama, J.

Chern. 34,2324 (1969). b. I. Kuwajima and E. Nakamura, J. Am. Chern. Soc. 97,3258 (1975). c. G. Stork and S. R. Dowd, Org. Synth. 55, 46 (1976); see also H. 0. House and B. M. Trost, J. Org. Chern. 30, 2502 (1965). d. G. Stork, P. Rosen, N. Goldman, R. V. Coombs and J. Tsuji, J. Am. Chern. Soc. 87, 275 (1965). alkoxides as bases. The presence of two electron-withdrawing substituents favors formation of a single enolate by removal of a proton from the carbon situated between them. Alkylation then occurs by an SN2 process.

19 The beauty of this technique is that it allows alkylation of 1,3-dicarbonyl compounds Ref. 19 to be carried out cleanly at the less activated position. Since, as discussed earlier, alkylation of the monoanion occurs at the carbon between the two carbonyl groups, the site of monoalkylation can be controlled by proper choice of the amount and nature of the base. This approach has significantly expanded the synthetic utility of enolate alkylations. A few examples of the formation and alkylation of dianions are collected in Scheme 1.

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