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

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

The two-part, 5th version of complex 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 past version, specially in computational chemistry. half B describes the main common and important artificial reactions, equipped at the foundation of response kind. it may stand-alone; jointly, with half A: constitution and Mechanisms, the 2 volumes supply a accomplished origin for the examine in natural chemistry. spouse web pages supply electronic types for college students and workout recommendations for teachers.

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Additional info for Advanced organic chemistry, part B: Reactions and synthesis

Example text

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. O. House, Org. , 52, 39 (1972). b. S. C. Welch and S. Chayabunjonglerd, J. Am. Chem. , 101, 6768 (1979).

O. House and M. J. Umen, J. Org. , 38, 1000 (1973). 26 CHAPTER 1 Alkylation of Enolates and Other Carbon Nucleophiles When an additional methyl substituent is placed at C(3), there is a strong preference for alkylation anti to the 3-methyl group. 1). 55 R' O– R' CH3 CH3 O– CH3 CH3 disfavored X CH3 CH3 O favored The enolates of 1- and 2-decalone derivatives provide further insight into the factors governing stereoselectivity in enolate alkylations. The 1(9)-enolate of 1-decalone shows a preference for alkylation to give the cis ring juncture, and this is believed to be due primarily a steric effect.

O O– C PhCH2 CH2 PhCH CH3 For cyclic ketones conformational factors also come into play in determining enolate composition. 2-Substituted cyclohexanones are kinetically deprotonated at the C(6) methylene group, whereas the more-substituted C(2) enolate is slightly favored at equilibrium (Entries 6 and 7). A 3-methyl group has a significant effect on the regiochemistry of kinetic deprotonation but very little effect on the thermodynamic stability of the isomeric enolates (Entry 8). 11 The synthetic importance of LDA and HMDS deprotonation has led to studies of enolate stereochemistry under various conditions.

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