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Advanced Organic Chemistry: Part B: Reactions and Synthesis - download pdf or read online

By Francis A. Carey

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 past version, specially in computational chemistry. half B describes the main common and helpful artificial reactions, equipped at the foundation of response variety. it might probably stand-alone; jointly, with half A: constitution and Mechanisms, the 2 volumes supply a entire beginning for the examine in natural chemistry. better half web content supply electronic versions for college students and workout ideas for instructors.

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Extra info for Advanced Organic Chemistry: Part B: Reactions and Synthesis

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For simple, conformationally biased cyc1ohexanone enolates such as that from 4-t-butycyc1ohexanone, there is little steric differentiation. The alkylation product is a nearly 1 : 1 mixture of the cis and trans isomers. - C,H,1 o (CH3)3C~ ~ C 2 H, 1 o (CH')'C4'H' H Ref. 20 The cis product must be formed through a transition state with a twistlike conformation to adhere to the requirements of stereoelectronic control. The fact that this pathway is not disfavored is consistent with other evidence that in enolate alkylations the transition state is early and reflects primarily the structural features of the reactant, not the product.

ENOLATES AND ENAMINES monomer is favored at high THF concentrations. 58 A crystal structure determination has been done on the lithiated N-phenylimine of methyl t-butyl ketone. It is a dimeric structure with the lithium cation positioned above the nitrogen and closer to the phenyl ring than to the ,a-carbon of the imine anion. 59 The structure is shown in Fig. 3. Just as enamines are more nucleophilic than enols, imine anions are more nucleophilic than enolates and react efficiently with alkyl halides.

Arn. Chern. Soc. 104, 1737 (1982). 8. 8. ALKYLATION OF ALDEHYDES, ESTERS, AM IDES, AND NITRILES 18 I I LOA, THF, -70·C H 3C CHJO>o 1) 4d cX9 LOA,OME 21 CH,=CH(CH,I,8r 31 lOA,OME 41 CH,I CH J (dO 0 : I "H II LOA • -;:? 21 CH,I, HMPA ::::,... H 0 I "H (82%) S" 11 2LOA THF, -78·C • 21 2CH,1. HMPA, -45·C 29 (65%1 11. OTMS (83%) (83%) a. T. R. Williams and L. M. Sirvio, J. Org. Chern. 45, 5082 (1980). b. M. W. Rathke and A. , J. Arn. Chern. Soc. 93,2320 (1971). C. S. C. Welch, A. S. C. Prakasa Rao, C.

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