Download Organic Reaction Mechanisms 2003: An Annual Survey Covering by A. C. Knipe PDF

By A. C. Knipe

So as to plan new natural syntheses the chemist has to appreciate natural response mechanisms. the most recent quantity during this sequence highlights the recent mechanisms released within the 2003 literature. An skilled crew of authors compiles those reports each year, in order that the reader can depend upon a continual caliber of choice and presentation.Content:
Chapter 1 Reactions of Aldehydes and Ketones and their Derivatives (pages 1–57): B. A. Murray
Chapter 2 Reactions of Carboxylic, Phosphoric and Sulfonic Acids and their Derivatives (pages 59–102): C. T. Bedford
Chapter three Oxidation and aid (pages 103–160): ok. ok. Banerji
Chapter four Carbenes and Nitrenes (pages 161–191): M. Christlieb, D. M Hodgson and E. Gras
Chapter five Nucleophilic fragrant Substitution (pages 193–204): M. R. Crampton
Chapter 6 Electrophilic fragrant Substitution (pages 205–222): R. G. Coombes
Chapter 7 Carbocations (pages 223–263): R. A. McClelland
Chapter eight Nucleophilic Aliphatic Substitution (pages 265–292): J. Shorter
Chapter nine Carbanions and Electrophilic Aliphatic Substitution (pages 293–331): M. L. Birsa
Chapter 10 removing Reactions (pages 333–353): A. C. Knipe
Chapter eleven Addition Reactions: Polar Addition (pages 355–426): P. Kocovsky
Chapter 12 Addition Reactions: Cycloaddition (pages 427–467): N. Dennis
Chapter thirteen Molecular Rearrangements: half 1 (pages 469–498): S. okay. Armstrong
Chapter 14 Molecular Rearrangements: half 2 (pages 499–560): J. M. Coxon

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359 ee ᭺ de ᭺ 1 Reactions of Aldehydes and Ketones and their Derivatives 39 While bridgehead enolates would appear to violate Bredt’s rule, examples are becoming more common, although they might be better termed α-keto carbanions. Several examples are described for a variety of carbonyl types, using medium ring sizes. For example, β-diketone (102) not only undergoes enolate formation when treated with lithium diisopropylamide at −105 ◦ C, but does so at the bridgehead position despite the presence of a well-activated methylene, as shown by a TMS chloride quench to give the substitution product (103).

341 A cross silyl benzoin reaction of an aldehyde (RCHO, R = aryl, alkyl, furyl) and an acylsilane (ArCOSiEt3 ) regioselectively yields a single α-hydroxy ketone in its silyl-protected form, ArCOCH(R)OSiEt3 . The reaction is catalysed by cyanide anion in ether solution, assisted by 18-crown-6. 344 Enolization and Related Reactions In Grignard addition of ethylmagnesium bromide to 1,2-diester (96), a remarkably stable enol (97) was isolated. The Grignard was added at −78 ◦ C, and aqueous quench under these conditions gives the expected ketone of (97), but bringing the magnesium alkoxide intermediate to room temperature before quenching results in the enol (97).

J. Org. , 2003, 4113. , and Amarnath, C. , Chem. , 138, 303672 (2003). , 44, 6867 (2003). Komarov, I. , Chem. Commun. (Cambridge), 2003, 2240. , Eur. J. Org. , 2003, 4016. Aggarwal, V. , Steele, R. , Ritmaleni, Barrell, J. , J. Org. , 68, 4087 (2003). Graham, M. , Wadsworth, A. , and Rayner, C. , Org. Biomol. , 1, 834 (2003). , 44, 1975 (2003). , and Mark´o, I. , Tetrahedron, 59, 8989 (2003). Belarmino, A. T. , Farah, J. P. , Bunton, C. , and Romsted, L. , J. Org. , 68, 706 (2003). , 44, 8623 (2003).

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