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

By Francis A. Carey

The two-part, 5th variation of complex 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, specifically in computational chemistry. half B describes the main basic and helpful artificial reactions, prepared at the foundation of response variety. it might probably stand-alone; jointly, with half A: constitution and Mechanisms, the 2 volumes offer a entire starting place for the learn in natural chemistry. significant other web content supply electronic versions for college students and workout ideas for instructors.

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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.

Chern. Soc. 94,4635 (1972); W. Nagata, M. Yoshioka, and M. Murakami, J. Am. Chern. Soc. 94, 4654 (1972). 47. For a review, see W. Nagata and M. Yoshioka, Org. React. 25, 255 (1977). Another very important method for adding a carbon chain at the {3-carbon atom of an a,{3-unsaturated carbonyl system involves organometallic reagents. This reaction will be discussed in Chapter 6. 10. 53'/,l \__)c~2CH2C02CH 3 CN 2b PhCH 2 CHCN I + H 2 C=CHCN NHJilt --------'+ I I PhCH 2CCH 2CH 2 CN (100'%:J CONH 2 CONH 2 3' + PhCH 2 N(CH 3 ) 3 .

M. Kaiser, W. G. Kenyon, and C. R. Hauser, Org. Snyth. 41, 72 (1967). R. P. Mariella and R. Raube, Org. Synth. IV, 288 (1963). M. J. Schlatter, Org. Synth. Ill, 223 (1955). K. F. Bernardy, J. F. Paletta, J. Nocera, P. Miranda, R. E. Schaub, and M. J. Weiss, J. Org. Chern. 45,4702 (1980). rates of the reaction are 650,000: 1 : 6500: 5 for formation of three-, four-, five-, . 1y. 13 . b ere d nngs, . respective an d stx-mem KO·t·Bu t-BuOH The preparation of 2-substituted {3-ketoesters (entries 1, 4, and 9) and 213.

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