By Francis A. Carey
The two-part, 5th version 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 past variation, particularly in computational chemistry. half B describes the main basic and valuable man made reactions, prepared at the foundation of response variety. it may well stand-alone; jointly, with half A: constitution and Mechanisms, the 2 volumes offer a accomplished starting place for the examine in natural chemistry. significant other web content offer electronic versions for college students and workout strategies for instructors.
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Additional info for Advanced Organic Chemistry: Part B: Reactions and Synthesis
9. Enamines, like enolate anions, are ambient nucleophiles. Alkylation at nitrogen is sometimes a competing reaction. The product of N -alkylation, after hydrolysis, leads to recovery of starting ketone. 0 H 20 R'X ---+ ---+ II RCCHR 2 Alkylation of enamines requires relatively reactive alkylating agents, such as methyl iodide, benzyl halides, a-haloketones, a-haloesters, and a-haloethers. 10. The nitrogen analogs of enolate ions, referred to as metalloenamines, can be prepared by deprotonation of imines: NR' NR' II II RC-CHR~ ~ RC-<;::R~ - -NR' I RC=CR1 Just as enamines are more nucleophilic than enols, metalloenamines are more nucleophilic than enolate anions and react efficiently with alkyl halides.
Prakasa Rao, C. G. Gibbs, and R. Y. Wong, J. Org. Chern. 45, 4077 (1980). W. H. Pirkle and P. E. Adams, J. Org. Chern. 45,4111 (1980). -M. Shieh and G. D. Prestwich, J. Org. Chern. 46,4319 (1981). of aldehyde enolates is rare because of the pronounced tendency of aldehydes to undergo aldol condensation (Chapter 2). Rapid and quantitative conversion of the aldehyde to the enolate is required in order to minimize aldol condensation, suggesting the use of very strong bases. Only a few examples of this approach have been reported.
Ginsburg, and R. Pappo, Org. React. 10, 179 (1950); J. W. Cornforth and R. Robinson, J. Chern. , 1855 (1949). 5. For more recent reviews of annulation reactions, see: a. R. E. Gawley, Synthesis 777 (1976). b. M. E. Jung, Tetrahedron 32, 3 (1976). c. B. P. Mundy, J. Chern. Ed. SO, 110 (1973). 1. Examples of the A. _-.. -~0 ,-m-+ II (CH 3 hC=CHCCH 3 (79%1 ao""'CCl B. __---+ ~ 7• s• ~ (CH 3 ),CCCH 3 + PhCHO NaOH ---'------+ ethanol- H 1 0 COCH 3 A + PhCHO KOH ~ V (90 %1 0 ?! (CH 3 ),CCCH=CHPh <90~~~ 0 II CCH=CHPh in which this alkylation-cyclization occurs are outlined below.