Issue 32 November 2009

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New Deoxofluorination Reagent

This paper from a Canadian company called OmegaChem describes the use of a family of novel reagents for deoxofluorination that offer advantages over reagents such as DAST and Deoxofluor.

A Liquid Reagent for Reductive Amination

Pyridine-borane complex (py:BH3) is fairly well known as a good reagent for effecting reductive amination, but a new analogous reagent, 5-ethyl-2-methylpyridine-borane complex (PEMB) is available.

Ortho Formylation

A simple way of formylating phenols is using paraformaldehyde, combined with anhydrous magnesium chloride and triethylamine in refluxing THF.

An Automated-Flow Microreactor for 100g synthesis using the Sonogashira reaction

Chemists at the synthetic chemistry department at Shionogi in Japan have reported the use of an automated microreactor system to quickly optimise the conditions for a complex Sonogashira reaction and to produce 100g quantities in as little as 50 hours.

Chiral Diene Ligands for Asymmetric Catalysis

The groups of Hayashi atKyoto and Carreira in Switzerland have pioneered the use of chiral diene catalysts, mostly based on bicyclic systems, such as bicyclo[2.2.1]heptadienes and bicyclo[2.2.2]octadienes and related systems.

Stereospecific C-H Oxidation by Hydrogen Peroxide using Iron Catalyst

A group at the University of Girona in Spain has developed unusual bio-inspired multi-amino catalysts, which allow the oxidation of C-H to C-OH at tertiary centres stereospecifically (Gómez L et al Angew Chem Int Ed, 2009, 48, 5720-3).

C-H Hydroxylation using a Heterocyclic Catalyst

In contrast to the previous highlight, the group of Du Bois at Stanford, USA have concentrated on designing oxaziridine catalysts which can effect similar hydroxylations (Litvinas N D et al, Angew Chem Int Ed, 2009, 48, 4513-6).

ChemTube3D - Interactive 3D Organic Reaction Mechanisms

ChemTube3D is a freely available web site based at the University of Liverpool aimed at students, lecturers and practising chemists. It contains interactive 3D animations for most of the important organic reactions covered during an undergraduate chemistry degree with supporting information on reactivity and spectroscopy. This provides a unique view of organic reaction mechanisms and surprising insight.

A Mechanistic Puzzle

An interesting formation of the piperidine ring occurs when the alkynamine is oxidised with m-CPBA, the initial N-oxide undergoing quite a few changes before the final product is formed.

Books

Flash Chemistry – Fast Organic Synthesis in Microsystems

Catalysis of Organic Reactions

... and finally - you might be an engineer if......
... ... you look forward to Christmas so you can put the kids' toys together.