Advanced Organic Chemistry: Part B: Reactions and Synthesis by Francis A. Carey

By Francis A. Carey

The two-part, 5th variation of complicated natural Chemistry has been considerably revised and reorganized for higher readability. the fabric has been up to date to mirror advances within the box because the prior variation, particularly in computational chemistry. half B describes the main basic and worthwhile man made reactions, geared up at the foundation of response kind. it will possibly stand-alone; jointly, with half A: constitution and Mechanisms, the 2 volumes offer a complete beginning for the research in natural chemistry. significant other web pages supply electronic types for college students and workout suggestions for instructors.

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Ref. PhCH2 H~CH20CH3 H2N (CH'hCH~H NH2 (CH')3C02C PhCH2 Ht-CH20CH3 H2N a. b. c. d. S. Hashimoto and K. Koga, Tetrahedron Lett, 573 (1978). A. I. Meyers, D. R. Williams, G. W. Erickson, S. White, and M. Druelinger, J. Am. Chem. Soc. 103,3081 (1981). K. Tomloka, K. Ando, Y. Takemasa, and K. Koga, J. Am. Chem. Soc. 106,2718 (1984). A. I. Meyers, D. R. Williams, S. White, and G. W Erickson, J. Am. Chem. Soc. 103, 3088 (1981). The anion of cyclohexanone N, N -dimethylhydrazone shows a strong preference for axial alkylation.

Chern. 53, 477 (1988). g. G. Stork, J. O. Gardner, R. K. , and K. A. Parker, J. Arn. Chern. Soc. 95, 2014 (1973). 30 CHAPTER 1 ALKYLATION OF NUCLEOPHILIC CARBON. ENOLATES AND ENAMINES In 4 the upper face is shielded by the isopropyl group while in 5 the lower face is shielded by the methyl and phenyl groups. As a result, alkylation of the two derivatives gives products of the opposite configuration. Subsequent hydrolysis or alcoholysis provides acids or esters in enantiomerically enriched form.

6 CHAPTER 1 ALKYLATION OF NUCLEOPHILIC CARBON. ENOLATES AND ENAMINES Kmetlc control of Isomenc enolate composition One the other hand, if enolates A and B can be interconverted rapidly, equilibrium will be established and the product composition will reflect the relative thermodynamic stability of the enolates. The enolate ratio is then governed by thermodynamic control. [A] -=K [8] 8 Thermodynamic control of Isomenc enolate compOSItion By adjusting the conditions under which an enol ate mixture is formed from a ketone, it is possible to establish either kinetic or thermodynamic control.

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