By Carey F.A., Sundberg R.J.
The two-part, 5th variation of complex 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 common and important artificial reactions, equipped at the foundation of response variety. it could possibly stand-alone; jointly, with half A: constitution and Mechanisms, the 2 volumes offer a finished beginning for the examine in natural chemistry. better half web content supply electronic types for college students and workout strategies for teachers.
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The two-part, 5th version of complicated natural Chemistry has been considerably revised and reorganized for higher readability. the cloth has been up-to-date to mirror advances within the box because the earlier version, specifically in computational chemistry. half B describes the main normal and precious man made reactions, prepared at the foundation of response kind.
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Extra resources for Advanced organic chemistry, part B: Reactions and synthesis
Transition structures for syn and anti attack on the kinetic enolate of trans-2,3dimethylcyclopentanone showing the staggered versus eclipsed nature of the newly forming bond. Reproduced from J. Am. Chem. , 121, 5334 (1999), by permission of the American Chemical Society. minor O– CH3 L M H CH3I L CH3 M O H CH3 major CH3 L O + M H CH3 minor major major:minor L = Ph, M = CH3 60:40 L = i-Pr, M = CH3 75:25 CH3 CH3 L CH3 M O L CH3 M O Ref. 60 These examples illustrate the issues that must be considered in analyzing the stereoselectivity of enolate alkylation.
F. A. B. Smith, III, and R. Mewshaw, J. Org. , 49, 3685 (1984). g. Y. L. Li, C. Huang, W. Li, and Y. Li, Synth. , 27, 4341 (1997). h. H. A. Smith, B. J. L. Huff, W. J. Powers, III, and D. Caine, J. Org. , 32, 2851 (1967). i. D. Caine, S. T. Chao, and H. A. Smith, Org. , 56, 52 (1977). j. G. Stork, P. Rosen, N. Goldman, R. V. Coombs, and J. Tsujii, J. Am. Chem. , 87, 275 (1965). to the more-substituted enolate precedes alkylation. Entries 3 and 4 show regiospecific generation of enolates by reaction of silyl enol ethers with methyllithium.
T. Hung, J. B. Nerenberg, and S. L. Schreiber, J. Am. Chem. , 118, 11054 (1996); D. L. Clark and C. H. Heathcock, J. Org. , 58, 5878 (1993). 5. (Continued) 7g O O Alkylation of Enolates and Other Carbon Nucleophiles I 1) LDA, –78°C CH3 (CH3)2CHCCH3 CH3 O–Li+ O 8h CH3 O2CCH3 CH 3 O CH3 CH3 Li, NH 3 CH3I CH3 CH3 O + CH3 60% 9i CH2 Li, NH3 CH2CH O NH3 CH2 H CH3(CH2)3I Li 10 CH3 CH3 CH3 45% trans/cis~20/1 H j 61% 2% CHCH2Br CH3 CH3 O2CCH3 CH3 O O–Li+ O CH3 Li+–O O H (CH2)3CH3 H 43% a. M. Gall and H.
Advanced organic chemistry, part B: Reactions and synthesis by Carey F.A., Sundberg R.J.