By Francis A. Carey
The two-part, 5th version 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 earlier version, specially in computational chemistry. half B describes the main common and helpful man made reactions, equipped at the foundation of response sort. it may well stand-alone; jointly, with half A: constitution and Mechanisms, the 2 volumes offer a finished beginning for the research in natural chemistry. better half web pages offer electronic types for college kids and workout ideas for instructors.
Read or Download Advanced Organic Chemistry: Part B: Reactions and Synthesis PDF
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Extra resources for Advanced Organic Chemistry: Part B: Reactions and Synthesis
A. I. Meyers, D. R. Williams, G. W. Erickson, S. White, and M. Druelinger, J. Am. Chem. Soc. 103,3081 (1981). K. Tomloka, K. Ando, Y. Takemasa, and K. Koga, J. Am. Chem. Soc. 106,2718 (1984). A. I. Meyers, D. R. Williams, S. White, and G. W Erickson, J. Am. Chem. Soc. 103, 3088 (1981). The anion of cyclohexanone N, N -dimethylhydrazone shows a strong preference for axial alkylation. 68 2-Methylcyclohexanone N,N-dimethylhydrazone is alkylated by methyl iodide to give cis-2,6-dimethylcyclohexanone.
Muller, F. Previdoli, and H. Desilvestro, Helv. Chim. Acta 64, 2497 (1981); J. E. Anderson, D. Casarini, and L. Lunazzi, Tetrahedron Lett. 29, 3141 (1988). 56. P. L. Stotter and K. A. Hill, J. Am. Chern. Soc. 96, 6524 (1974). 9. 9. THE NITROGEN ANALOGS OF ENOLS AND ENOLATESENAMINES AND IMINE ANIONS pyrrohdme CH,=CHCH,Br 3)H,O I) 2) 3· I) pyrrohdme 2) MeCOCHBrMe 3)H,O I) I (31 %) pyrrohdme 2) Mel 3)H,O 5" 1) pyrrohdine 2) CH 2 =CCH 2C1. NaJ. CI dllsopropylamine 3) H 2 0 a. G. Stork. A. Brizzolara.
A late transition state should disfavor the formation of the cis isomer because of the strain energy associated with the initial non chair conformation of the product. The introduction of an alkyl substituent at the a-carbon in the enolate enhances stereoselectivity somewhat. This is attributed to a steric effect in the enolate. To minimize steric interaction with the solvated oxygen, the alkyl group is distorted somewhat from coplanarity. This biases the enolate toward attack from the axial 20.