Advanced organic chemistry, part B: Reactions and synthesis by Carey F.A., Sundberg R.J. PDF

By Carey F.A., Sundberg R.J.

ISBN-10: 038768350X

ISBN-13: 9780387683508

The two-part, 5th version 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 past variation, specially in computational chemistry. half B describes the main basic and invaluable man made reactions, equipped at the foundation of response style. it could stand-alone; jointly, with half A: constitution and Mechanisms, the 2 volumes supply a finished starting place for the examine in natural chemistry. better half web pages supply electronic versions for college kids and workout suggestions for teachers.

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Seebach, Angew. Chem. Int. Ed. , 27, 1624 (1988). E. H. Amonoco-Neizer, R. A. Shaw, D. O. Skovlin, and B. C. Smith, J. Chem. , 2997 (1965); C. R. Kruger and E. G. Rochow, J. Organomet. , 1, 476 (1964). R. R. Fraser and T. S. Mansour, J. Org. , 49, 3442 (1984). M. W. Rathke and R. Kow, J. Am. Chem. , 94, 6854 (1972); R. A. Olofson and C. M. Dougherty, J. Am. Chem. , 95, 581, 582 (1973). E. J. Corey and M. Chaykovsky, J. Am. Chem. , 87, 1345 (1965). C. A. Brown, J. Org. , 39, 1324 (1974); R. Pi, T.

Chem. Soc. , 77, 259 (2004); M. Suzuki, H. Koyama, and R. Noyori, Tetrahedron, 60, 1571 (2004). C. L. Liotta and T. C. , 26, 1599 (1985). 46 These results, too, are presumably due to disaggregation of the enolate by the polyamines. 2 O OLi PhCH2Br Alkylation of Enolates CH2Ph 40 min, – 23°C Additive (3eq) none HMPA DMPU Yield (%) 6 34 3 Me2NCH2CH2NMe2 6 (Me2NCH2CH2)2NMe 50 (Me2NCH2CH2NCH2)2 72 Me Me2N(CH2CH2N)3CH2CH2NMe2 33 Me The reactivity of enolates is also affected by the metal counterion.

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. 64 Entries 5 and 6 illustrate this method.

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Advanced organic chemistry, part B: Reactions and synthesis by Carey F.A., Sundberg R.J.


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