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 larger readability. the cloth has been up to date to mirror advances within the box because the earlier variation, specifically in computational chemistry. half B describes the main common and priceless artificial reactions, prepared at the foundation of response style. it may possibly stand-alone; jointly, with half A: constitution and Mechanisms, the 2 volumes offer a finished beginning for the research in natural chemistry. spouse web content supply electronic versions for college kids and workout recommendations for instructors.

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THF, -78"C 2J 2CH 3 1·, HMPA, -45"C 0 a. b. c. d. e. (82%) CH,J:) (65%) 0 T. R. Williams and L. M. Sirvio, J. Org. Chern. 45, 5082 (1980). M. W. Rathke and A. , J. Am. Chern. Soc. 93,2320 (1971). C. Welch, A. C. 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).

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. 4. These reactions are all mechanistically similar in that a carbanion, formed by deprotonation using a suitable base, attacks an electrophilic substrate in an SN2 manner.

M. W. Rathke and D. , 4249 (1972). 24 Alkylation also takes place selectively at the a-carbon: CHAPTER 1 ALKYLATION OF NUCLEOPHILIC CARBON· ENOLATES AND ENAMINES CH 3 CH 3 0 0 II "- /3 / " NaNH II C=CHCCH 3 + CH 2 =CHC=CHCH 2 Br ---4 CHz=CHC=CHCH 2 -CHCCH 3 " I CH 3 I I NH, Ref. 9 C CH 3 y CH 3 188 % 1 /13~ y CH 2 Phenoxide ions offer opportunities for C- or 0-alkylation which are closely balanced: 0 0 In this case, C-alkylation is burdened energetically by the fact that aromaticity is destroyed as C-alkylation proceeds: a O--+ & o~ OH ~ R The effect of solvent on the site of alkylation has been clearly demonstrated.

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