By Francis A. Carey

The two-part, 5th variation of complicated natural Chemistry has been considerably revised and reorganized for better readability. the fabric has been up-to-date to mirror advances within the box because the prior variation, specially in computational chemistry. half B describes the main normal and invaluable man made reactions, equipped at the foundation of response style. it could possibly stand-alone; jointly, with half A: constitution and Mechanisms, the 2 volumes supply a entire beginning for the research in natural chemistry. significant other web pages supply electronic types for college kids and workout ideas for instructors.

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Additional info for Part B: Reactions and Synthesis

Example text

P. Beletskaya, and 0. A. Reutov, Dokl. Akad. Nauk. SSR (Engl. ) 187:595 (1969). Higher C/O-alkylation mtios are observed with alkyl halides than with alkyl sulfonates and sulfates. The highest C/O-alkylation ratios are obtained with alkyl iodides. For ethylation of the potassium salt of ethyl acetoacetate in HMPA, the product compositions shown below were obtained. 48 Of the two nucleophilic sites in an enolate ion, oxygen is harder than carbon. Nucleophilic substitution reactions of the SN2 type proceed best when the nucleophile and leaving group are either both hard or both soft.

102 Hydrolysis of this intermediate regenerates the carbonyl group. 103 W oTMs I+ CH3 H 20 o- Other Lewis acids can also effect conjugate addition of silyl enol ethers to electrophilic alkenes. For example, Mg(Cl04 h catalyzes addition of ketene silyl acetals: Ref. 104 Lanthanide salts have been found to catalyze addition of rx-nitroesters, even in aqueous solution. 105 TH3 ~ CH302CCCHzCHzCCH3 I 99% Ref. 106 NOz 98. 99. 100. 101. 102. 103. 104. 105. 106. C. H. Heathcock, M. M. Hansen, R. B. Ruggeri, and J.

M. Trost, J. Org. Chem. 30:2502 (1965). stereoselectivity because a steric interaction with the solvated enolate oxygen distorts the enolate in such a way as to favor the axial attack. 37 The placement of an axial methyl group at C-10 in a 2(1)-decalone enolate introduces a 1,3-diaxial interaction with the approaching electrophile. The preferred alkylation product results from approach on the upper face of the enolate. ~cr R'-x The prediction and interpretation of alkylation stereochemistry also depends on consideration of conformational effects in the enolate.

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