Organic Reaction Mechanisms · 2009: An annual survey by A. C. Knipe

By A. C. Knipe

Organic response Mechanisms 2009, the forty fifth  annual quantity during this hugely winning and certain sequence, surveys learn on natural response mechanisms defined within the to be had literature dated 2009.  the subsequent periods of natural response mechanisms are comprehensively reviewed:

• Reaction of Aldehydes and Ketones and their Derivatives
• Reactions of Carboxylic, Phosphoric, and Sulfonic Acids and their Derivatives
• Oxidation and relief
• Carbenes and Nitrenes
• Nucleophilic fragrant Substitution
• Electrophilic fragrant Substitution
• Carbocations
• Nucleophilic Aliphatic Substitution
• Carbanions and Electrophilic Aliphatic Substitution
• Elimination Reactions
• Polar Addition Reactions
• Cycloaddition Reactions
• Molecular Rearrangements

An skilled group of authors bring together those reports each year, in order that the reader can depend upon a continuous caliber of choice and presentation.  This quantity features a 5-year cumulative index.

Content:
Chapter 1 Reactions of Aldehydes and Ketones and their Derivatives (pages 1–73): B. A. Murray
Chapter 2 Reactions of Carboxylic, Phosphoric, and Sulfonic Acids and their Derivatives (pages 75–115): C. T. Bedford
Chapter three Oxidation and relief (pages 117–190): R. N. Mehrotra
Chapter four Carbenes and Nitrenes (pages 191–214): E. Gras
Chapter five Nucleophilic fragrant Substitution (pages 215–228): M. R. Crampton
Chapter 6 Electrophilic fragrant Substitution (pages 229–256): R. G. Coombes
Chapter 7 Carbocations (pages 257–273): R. A. McClelland
Chapter eight Nucleophilic Aliphatic Substitution (pages 275–310): ok. C. Westaway
Chapter nine Carbanions and Electrophilic Aliphatic Substitution (pages 311–334): M. L. Birsa
Chapter 10 removal Reactions (pages 335–346): M. L. Birsa
Chapter eleven Addition Reactions: Polar Addition (pages 347–419): P. Kocovsky
Chapter 12 Addition Reactions: Cycloaddition (pages 421–456): N. Dennis
Chapter thirteen Molecular Rearrangements: half 1. Pericyclic Molecular Rearrangements (pages 457–481): S. okay. Armstrong
Chapter 14 Molecular Rearrangements: half 2 (pages 483–530): J. M. Coxon

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Additional resources for Organic Reaction Mechanisms · 2009: An annual survey covering the literature dated January to December 2009

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G. F or NCS) has been used to help design better asymmetric catalysts. Using kinetic and MS studies, parallel mono- and bimetallic pathways have been distinguished. The latter case involves cooperative catalysis by two vanadiums in different oxidation states, allowing simultaneous activation of aldehyde and cyanide reactants. 405 A multi-method theoretical study has probed the mechanism and enantioselectivity of hydrocyanation of aromatic aldehydes with a peptide catalyst, cyclo[(S)-His-(S)Phe].

105) with up to 99% ee, using potassium aryltriolborates, catalysed by ee ee 45 1 Reactions of Aldehydes and Ketones and their Derivatives nickel bis(cyclooctadiene) and a duphos auxiliary. 380 PhMe2Si OH OH R3 R (105) NHR4 ∗ R1 ee OMe CHO R2 (106) (107) Thiophenyl methanols, Ar1∗ CHOHAr2 (Ar1 = phenyl, substituted phenyl, naphthyl, furyl; Ar2 = 2-thiophenyl), have been prepared with up to 96% ee, via asymmetric addition of thiophenylboronic acid to aldehydes in the presence of diethylzinc. 382 Aluminium reagents of the form AlArEt2 (THF) efficiently arylate aldehydes under mild conditions, with high enantioselectivity, using a titanium(IV) complex of (R)−H8 −BINOL as a chiral catalyst.

Ketones also work [giving spiro-products, and changing the hydroxyl in (93) to tosylamino sets up the corresponding aza-Prins process] to give isoquinolines. g. 95) have been prepared from a hydroxy(allenylmethyl)silane (96) and aromatic aldehydes via an intermolecular double Prins-type cyclization. e. 348 The Biginelli synthesis of pyrimidines, from benzaldehyde, acetoacetate, and urea (or thiourea), has been investigated by ESI-MS and -MS/MS, supported by DFT calculations. 349 A new cascade reaction has been used to combine carbonyl compounds with malononitrile to give 1,1,2,2-tetracyanocyclopropanes.

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